Methyl iodide → HCID 22674302, compound

HRID 1005986Notes

Reaction equation

CI.FC(F)(F)C(O)=O.C(O[C:15](=O)[NH:16][C:17]1[C:18]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[N:19][C:20]([S:23][CH3:24])=[N:21][CH:22]=1)(C)(C)C.C(O)(C)(C)C.[F:39][C:40]([F:58])([F:57])[C:41]1[CH:42]=[C:43]([C:51]([CH3:56])([CH3:55])[C:52](Cl)=[O:53])[CH:44]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:46]=1>>[F:39][C:40]([F:58])([F:57])[C:41]1[CH:42]=[C:43]([C:51]([CH3:56])([CH3:55])[C:52]([N:16]([C:17]2[C:18]([O:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[N:19][C:20]([S:23][CH3:24])=[N:21][CH:22]=2)[CH3:15])=[O:53])[CH:44]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:46]=1

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 6422Trifluoroacetic acid

HCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chloride

HCID 131724584HCID 131724584, compound

Product 1

HCID 22674302HCID 22674302, compound

Procedure

In an analougous manner to that described in Examle 46 a) there was obtained from 4-(4-fluoro-phenoxy)-2-methylsulfanyl-pyrimidine-5-carboxylic acid, diphenylphosporylazide and t-butanol [4-(4-fluoro-phenoxy)-2-methylsulfanyl-pyrimidin-5-yl]-carbamic acid tert.-butyl ester, which was methylated with methyliodide and than deprotected with trifluoracetic acid according to Example 43b)c). The resulting [4-(4-fluoro-phenoxy)-2-methylsulfanyl-pyrimidin-5-yl]-methyl-amine was treated with 2-(3,5-bis-trifluormethyl-phenyl)-2-methyl-propionyl chloride as described in Example 43e) to give 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(4-fluoro-phenoxy)-2-methylsulfanyl-pyrimidin-5-yl]-N-methyl-isobutyramide as a white foam, MS (EI): 547 (M+).

Sources & evidence

ORD record: ord-5e7d9b59bf124719b627d77461197e0c
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787539B2

Reaction notes

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