2-Chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinothieno[2,3-d]pyrimidine → HCID 58233875, compound

HRID 881496Notes

Reaction equation

HRID 881496 reaction equation
C([SiH2][O:6][C:7](C1C=CC=CC=1)(C1C=CC=CC=1)[C:8]1[CH:13]=[CH:12][C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][N:9]=1)(C)(C)C.Cl[C:36]1[N:37]=[C:38]([N:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)[C:39]2[CH:44]=[C:43]([CH2:45][N:46]3[CH2:51][CH2:50][N:49]([S:52]([CH3:55])(=[O:54])=[O:53])[CH2:48][CH2:47]3)[S:42][C:40]=2[N:41]=1>>[CH3:55][S:52]([N:49]1[CH2:50][CH2:51][N:46]([CH2:45][C:43]2[S:42][C:40]3[N:41]=[C:36]([C:11]4[CH:12]=[CH:13][C:8]([CH2:7][OH:6])=[N:9][CH:10]=4)[N:37]=[C:38]([N:56]4[CH2:57][CH2:58][O:59][CH2:60][CH2:61]4)[C:39]=3[CH:44]=2)[CH2:47][CH2:48]1)(=[O:54])=[O:53]

Participants

3

Reactant 2

HCID 568339462-Chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinothieno[2,3-d]pyrimidineHCID 131728702HCID 131728702, compound

Product 1

HCID 58233875HCID 58233875, compound

Procedure

2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine was reacted with 2-chloro-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[2,3-d]pyrimidine in General Procedure A. Purification on silica yielded 362. NMR: (CDCl3): 2.58-2.60 (4H, m), 2.73 (3H, s, Me), 3.20-3.22 (4H, m), 3.75 (2 μl, s), 3.81-3.84 (4H, m), 3.90-3.92 (4H, m), 4.76 (2H, s, NH2), 6.92 (1H, s, Ar), 7.25 (1H, d, J 8.3, Ar), 8.61 (1H, d, J 8.3, Ar) and 9.51 (1H, s, Ar). MS: (ESI+): MH+=505.14

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-dfae7ff178e84889ace42226101872a2
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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