4-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amine → 4-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amine

HRID 391038Notes

Reaction equation

HRID 391038 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]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)=[CH:8][C:6]=2[N:7]=1.[CH3:29][C:30]1[C:35]([B:36]2[O:40][C:39]([CH3:42])([CH3:41])[C:38]([CH3:44])([CH3:43])[O:37]2)=[CH:34][N:33]=[C:32]([NH2:45])[N:31]=1>>[CH3:29][C:30]1[C:35]([B:36]2[O:40][C:39]([CH3:41])([CH3:42])[C:38]([CH3:44])([CH3:43])[O:37]2)=[CH:34][N:33]=[C:32]([NH2:45])[N:31]=1.[NH2:45][C:32]1[N:31]=[C:30]([CH3:29])[C:35]([C:2]2[N:3]=[C:4]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]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)=[CH:8][C:6]=3[N:7]=2)=[CH:34][N:33]=1

Participants

4

Reactant 2

HCID 529879064-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amineHCID 866235471-[4-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]-2-hydroxypropan-1-one

Product 2

HCID 529879064-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amineHCID 58233849(S)-1-(4-((2-(2-Amino-4-methylpyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one

Procedure

4-methyl-5-(4,4,5,5-tetramethyl (1,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine was prepared according to WO2007/084786. 110 mg of 1-[4-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]-2-hydroxypropan-1-one was coupled to 4-methyl-5-(4,4,5,5-tetramethyl (1,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine via General Procedure A to yield 50 mg of 324. MS (Q1) 499.2 (M)+.

Sources & evidence

ORD record
ord-9523afda412148c3bc1e7420de26a85a
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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