4-Chloro-1-(2-chlorophenyl)-1H-pyrazolo[3,4-D]pyrimidine → Methyl (2S)-3-[2-(tert-butyl-diphenylsilyl)oxyethoxy]-2-[1-(2-chlorophenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxypropanoate

HRID 1098187Notes

Reaction equation

HRID 1098187 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][O:21][CH2:22][C@H:23]([OH:28])[C:24]([O:26][CH3:27])=[O:25])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:30]1[N:35]=[CH:34][N:33]=[C:32]2[N:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[Cl:45])[N:37]=[CH:38][C:31]=12>>[Si:1]([O:18][CH2:19][CH2:20][O:21][CH2:22][C@H:23]([O:28][C:30]1[C:31]2[CH:38]=[N:37][N:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[Cl:45])[C:32]=2[N:33]=[CH:34][N:35]=1)[C:24]([O:26][CH3:27])=[O:25])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 112655704-Chloro-1-(2-chlorophenyl)-1H-pyrazolo[3,4-D]pyrimidine2×HCID 59279512(S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-hydroxypropanoate

Product 1

HCID 57504664Methyl (2S)-3-[2-(tert-butyl-diphenylsilyl)oxyethoxy]-2-[1-(2-chlorophenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxypropanoate

Procedure

Prepared according to the method for Intermediate AE2 from (S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-hydroxypropanoate (Intermediate AB3) and 4-chloro-1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine (Intermediate B1). 1H NMR (400 MHz, DMSO) δ 0.94 (9H, s), 3.56-3.75 (4H, m), 3.68 (3H, s), 3.90-4.09 (2H, m), 5.80-5.85 (1H, m), 7.29-7.43 (6H, m), 7.50-7.67 (7H, m), 7.67-7.74 (1H, m), 8.43 (1H, s), 8.52 (1H, s); m/z (ESI+) (M+H)+=631; HPLC tR=3.38 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f73361daf6004502a8633c49885a1696
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

Loading…