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Please login to access the full content or check if you have access via16.12.4.1.4.4.1 Method 1: Reaction of Halopyrimidines with Thiolates
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von Angerer, S., Science of Synthesis, (2004) 16, 520.
Although several examples for the substitution of halogens by alkylthiolates are known[561,567,654,668,672,673] the preferred route of synthesis involves the alkylation of the corresponding pyrimidinethiols. (Arylsulfanyl)pyrimidines, however, are generally prepared by a nucleophilic substitution reaction of the halopyrimidine with the thiophenolate.[558,674] The (trifluoromethyl)sulfanyl group can be introduced into the 6-position of tetrafluoropyrimidine by reaction with thiocarbonyl difluoride in the presence of cesium fluoride.[675] Examples for the substitution of halopyrimidines by metal thiolates are listed in Table 10.
Meeee 88 Meeeeeeeee ee Meeeeeeeeeeeeee eeee (Meeeeeeeeeeee)- eee (Meeeeeeeeeee)eeeeeeeeeee[888,888,888,888,888,888–888]
Meeeeeeee | Meeeeee | Meeeeee | Meeee (%) | ee (°M) ee ee (°M/Meee) | Mee |
---|---|---|---|---|---|
MeMM, e-MeMM, MMM, ee, 8 e | 88 | 88 | [888] | ||
MeMM, e-MeMM, MeMM, ee, 88 e | 88 | 88 | [888] | ||
MeMMe, MMM, 88°M, 8 e | 88 | 88 | [888] | ||
MeMMe, eeeeeee, eeeeee, 88 e | 88 | eee | [888] | ||
MeMMe, eeeeeee, eeeeee, 88 e | 88 | 88/8.88 | [888] | ||
MeMMe, MeMM, 8°M, 8 e | 88 | 888–888/8 | [888] | ||
MeMM, Me8M, MeMM, eeeeee, 88 e | 88 | 888–888 | [888] | ||
8-MeM8M8MM, MeMM, MeMM, ee, 88 eee | 88 | 888–888 | [888] |
References
[558] | Meeeee, M. M.; Meeeeeee, M. M., Meee. M. Meee., (8888) 88, 8888. |
[561] | Meee, M.; Meeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[567] | Meeee, M.; Meeeeee, M., Meee Meee. Meeee., Mee. M, (8888) 88, 888. |
[654] | Meeee, M. M.; Meeeee, M., Meee. M. Meee., (8888) 88, 888. |
[668] | Meeeeeee, M.; Meeeeee, M., Meee Meee. Meeee., Mee. M, (8888) 88, 888. |
[672] | Meeeeeeee, M.; Meeeeee, M.; Meee, M., Meeeeeeeeeee, (8888) 88, 888. |
[673] | Meeeeee, M.; Meeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[674] | Meeee, M. M.; Meeeee, M. M.; Meeeeeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[675] | Meeeeee, M.; Meee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 8e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.