2,4-Dimethoxypyrimidine-5-boronic acid pinacol ester → 2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholino-6-((4-N-phenylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidine

HRID 390953Notes

Reaction equation

HRID 390953 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.[CH3:33][O:34][C:35]1[N:40]=[C:39]([O:41][CH3:42])[C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][N:36]=1>>[CH3:33][O:34][C:35]1[N:40]=[C:39]([O:41][CH3:42])[C:38]([C:21]2[N:22]=[C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[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]=2)=[CH:37][N:36]=1

Participants

3

Reactant 2

HCID 162183882,4-Dimethoxypyrimidine-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 582338612-(2,4-dimethoxypyrimidin-5-yl)-4-morpholino-6-((4-N-phenylsulfonylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidine

Procedure

6-(4-Benzenesulfonyl-piperazin-1-ylmethyl)-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (described above) was reacted with 2,4-dimethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidine in General Procedure A. Purification on silica yielded 260. NMR (400 MHz, CDCl3): 2.56-2.58 (4H, m, CH2), 3.04 (4H, m, CH2), 3.74-3.77 (6H, m, CH2), 3.88-3.91 (4H, m, CH2), 3.98 (3H, s, CH3), 4.01 (3H, s, CH3), 7.21 (1H, s, ar), 7.47-7.51 (2H, m, ar), 7.54-7.58 (1H, m, ar), 7.71 (2H, d (J=7.13), ar), 8.84 (1H, s, ar). (M+H)+ 598.28

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-81ac16d70099454e904520fd989ecc62
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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