You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.16.17.3.4.5.3 Method 3: From Sulfanylpurines
Please login or sign up for a free trial to access the full content.
Seela, F.; Ramzaeva, N.; Rosemeyer, H., Science of Synthesis, (2004) 16, 1071.
(Methylsulfanyl)purines are good starting materials for the preparation of aminopurines. This method can be successfully employed for the synthesis of purin-6-amines, e.g. 239 (Scheme 135), from 6-(methylsulfanyl)purines, but presents some difficulties when the methylsulfanyl group is in the 2-position. Thus, the 2-(methylsulfanyl) group of 2-(methylsulfanyl)adenine could not be replaced successfully by ammonia under a variety of conditions and this experience was duplicated using alkylamines.[541] However, in the case of 2-(methylsulfanyl)purin-6-ol it is possible to perform the displacement reaction in an alcoholic amine solution (Me2NH, MeOH, 140°C, 24 h) to give 2-(methylamino)purin-6-ol in 61% yield.[623]
Mee eeeeeeeeeeee eeeeeeeeeeee eeeeeeee eee ee eeeeeeeeeee eeeee eeeeeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeeeee eeeeeee ee eee eeeeeeeeeeeeee eeeeeeeee. Meee, eeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeeeee eee eeeee eeeeeeee eee eeee eeeeeee eeee eee eeeeeeeeeee ee eeee eee eeeee eeeeeeeee.[888–888]
Meeeee 888 Meeee-8-eeeeee ee Meeeeeeee ee 8-(Meeeeeeeeeeeee)eeeeeee[888,888,888,888,888]
| M8 | M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|
| M | M | Me | M8M, 888°M, 88 e | 88 | [888] |
| M | Me | M | M8M, 888°M, 88 e | 88 | [888] |
| MM | M | M | M8M, 888°M, 8 e | 88 | [888] |
| M | M | Me | 888°M, 88 e | 88 | [888] |
| MM8 | M | Me | M8M, 888°M, 88 e | 88 | [888] |
| M | β-M-eeeeeeeeeeeee | M | MeMM, 888°M, 8 e | 88 | [888] |
| MM | β-M-eeeeeeeeeeeee | M | MeMM, 888°M, 8 e | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
M8-Meeeeeeeeeeee (888, M8 = M8 = M; M8 = Me):[888]
M eeeeeee ee 8-(eeeeeeeeeeeeee)eeeeee (8.88 e, 88.8 eeee) eee 88% ee MeMM8 (8 eM) eee eeeeee ee eeeeee eeee ee 888°M eee 88 e. Meeee eeeeeee, eee eeeeeee eee eeeeeeeeee ee eeeeeee eee eee eeeeeee eeeeeeeeeeeeee (M8M, 88 eM), eeeeeeeee eeeeeeee (eee eeeeeeeeeeeeee); eeeee: 8.8 e (88%).
References
| [236] | Meeeeeee, M.; Meeeeeeee, M.; Meeeeeeee, M.; Meeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
| [309] | Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [311] | Mee, M. M.; Meeeee, M.; Meeeeee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [541] | Meeeeee, M. M. M.; Meeee, M.; Meee, M. M.; Meeeee, M., M. Meee. Mee., (8888), 8888. |
| [623] | Meeee, M. M.; Meeee, M. M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
| [624] | Meee, M. M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [625] | Meeeeee, M. M.; Meeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
| [626] | Meeeeeee, M.; Meeeeeeee, M.; Meeeeeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
| [627] | Meeeee, M. M. M.; Meeee, M. M., Meeeeeeeeee, Meeeeeeeeee Meeeeee Meeee, (8888) 88, 8888. |
| [628] | Meeee, M. M.; Meeee, M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
| [629] | Meeeeeeeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 8e8, 888.
Return to Top