5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyrimidin-2-amine → 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyrimidin-2-amine

HRID 391039Notes

Reaction equation

HRID 391039 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18](=[O:22])[CH:19]([OH:21])[CH3:20])[CH2:14][CH2:13]3)=[C:8]([CH3:23])[C:6]=2[N:7]=1.[CH3:30][C:31]1([CH3:49])[C:35]([CH3:37])([CH3:36])[O:34][B:33]([C:38]2[C:39]([C:45]([F:48])([F:47])[F:46])=[N:40][C:41]([NH2:44])=[N:42][CH:43]=2)[O:32]1>>[CH3:36][C:35]1([CH3:37])[C:31]([CH3:30])([CH3:49])[O:32][B:33]([C:38]2[C:39]([C:45]([F:46])([F:47])[F:48])=[N:40][C:41]([NH2:44])=[N:42][CH:43]=2)[O:34]1.[NH2:44][C:41]1[N:40]=[C:39]([C:45]([F:48])([F:46])[F:47])[C:38]([C:2]2[N:3]=[C:4]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:5]3[S:10][C:9]([CH2:11][N:12]4[CH2:17][CH2:16][N:15]([C:18](=[O:22])[C@@H:19]([OH:21])[CH3:20])[CH2:14][CH2:13]4)=[C:8]([CH3:23])[C:6]=3[N:7]=2)=[CH:43][N:42]=1

Participants

4

Reactant 2

HCID 574164395-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyrimidin-2-amineHCID 866235481-[4-(2-Chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]-2-hydroxy-propan-1-one

Product 2

HCID 574164395-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyrimidin-2-amineHCID 58233939(S)-1-(4-((2-(2-Amino-4-(trifluoromethyl)pyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one

Procedure

5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-4-trifluoromethyl-pyrimidin-2-ylamine was prepared according to WO2007/084786. 110 mg of 1-[4-(2-Chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]-2-hydroxy-propan-1-one, prepared as in Example 118, was coupled to 5-(4, 4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-4-trifluoromethyl-pyrimidin-2-ylamine via General Procedure A to yield 20 mg of 325 MS (Q1) 567.2 (M)+.

Sources & evidence

ORD record
ord-446e4111c0ee4326832a6f8257d84b8d
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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