2-Aminopyrimidine-5-boronic acid, pinacol ester → 5-(4-Morpholino-6-((4-n-phenylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

HRID 390839Notes

Reaction equation

HRID 390839 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[S:25][C:24]4[C:23]([N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[N:22][C:21](Cl)=[N:20][C:19]=4[CH:18]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:33][C:34]1[N:39]=[CH:38][C:37](B2OC(C)(C)C(C)(C)O2)=[CH:36][N:35]=1>>[O:29]1[CH2:30][CH2:31][N:26]([C:23]2[C:24]3[S:25][C:17]([CH2:16][N:13]4[CH2:14][CH2:15][N:10]([S:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)(=[O:9])=[O:8])[CH2:11][CH2:12]4)=[CH:18][C:19]=3[N:20]=[C:21]([C:37]3[CH:36]=[N:35][C:34]([NH2:33])=[N:39][CH:38]=3)[N:22]=2)[CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 866235146-(4-Benzenesulfonyl-piperazin-1-ylmethyl)-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Product 1

HCID 582339155-(4-Morpholino-6-((4-n-phenylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

Procedure

6-(4-Benzenesulfonyl-piperazin-1-ylmethyl)-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine was reacted with 2-aminopyrimidine-5-boronic acid pinacol ester using General Procedure A. Purification on silica yielded 120. (400 MHz, CDCl3): 2.56-2.58 (4H, m, CH2), 3.04 (4H, m, CH2), 3.74 (2H, s, CH2), 3.76-3.79 (4H, m, CH2), 3.90-3.92 (4H, m, CH2), 7.18 (1H, s, ar), 7.47-7.51 (1H, d (J=7.36), ar), 7.55 (1H, d (J=7.36), ar), 7.71 (2H, d (J=7.07), ar), 9.19 (2H, s, ar). (M+H)+ 553.29

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-9998d67e6df947e6a383da9e48885bd9
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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