Methyl iodide → HCID 22674317, compound

HRID 1005991Notes

Reaction equation

CI.FC(F)(F)C(O)=O.C(O[C:15](=O)[NH:16][C:17]1[C:18]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])=[N:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:21][CH:22]=1)(C)(C)C.C(O)(C)(C)C.[F:43][C:44]([F:62])([F:61])[C:45]1[CH:46]=[C:47]([C:55]([CH3:60])([CH3:59])[C:56](Cl)=[O:57])[CH:48]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:50]=1>>[F:43][C:44]([F:62])([F:61])[C:45]1[CH:46]=[C:47]([C:55]([CH3:60])([CH3:59])[C:56]([N:16]([CH3:15])[C:17]2[C:18]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH3:36])=[N:19][C:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:21][CH:22]=2)=[O:57])[CH:48]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:50]=1

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 6422Trifluoroacetic acid

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

HCID 131724585HCID 131724585, compound

Product 1

HCID 22674317HCID 22674317, compound

Procedure

In an analougous manner to that described in Examle 72 a) there was obtained from 2-phenyl-4-o-tolyloxy-pyrimidine-5-carboxylic acid, diphenylphosphorylazide and t-butanol (2-phenyl-4-o-tolyloxy-pyrimidin-5-yl)-carbamic acid tert.-butyl ester, which was methylated with methyliodide and than deprotected with trifluoracetic acid according to Example 72 b) c). The resulting methyl-(2-phenyl-4-o-tolyloxy-pyrimidin-5-yl)-amine was treated with 2-(3,5-bis-trifluormethyl-phenyl)-2-methyl-propionyl chloride as described in Example 72 e) to give 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(2-phenyl-4-o-tolyloxy-pyrimidin-5-yl)-isobutyramide as a white foam, MS (ISP): 574.1 (M+H)+.

Sources & evidence

ORD record: ord-29a7df29968043ec83627ab0dd291ca4
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787539B2

Reaction notes

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