4-chloro-1-(3-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine → (2S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(3-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate

HRID 1098185Notes

Reaction equation

HRID 1098185 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]=[C:41]([F:45])[C:40]=3[CH3:46])[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[N:35]=[CH:34][N:33]=[C:32]2[N:36]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[C:40]=3[CH3:46])[N:37]=[CH:38][C:31]=12)[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 575046614-chloro-1-(3-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidineHCID 59279512(S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-hydroxypropanoate

Product 1

HCID 59279546(2S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(3-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate

Procedure

Prepared using a procedure analogous to that described for Intermediate AE2 using (S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-hydroxypropanoate (Intermediate AB3) and 4-chloro-1-(3-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine (Intermediate AF5). 1H NMR (400 MHz, DMSO) d 0.94 (9H, s), 1.96 (3H, d), 3.81-3.63 (7H, m), 4.09-4.02 (1H, m), 4.13 (1H, m), 5.89 (1H, m), 7.50-7.30 (9H, m), 7.63 (4H, m), 8.49 (1H, s), 8.59 (1H, s). m/z (ES+) (M+H)+=629; HPLC tR=3.43 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3bba79c4d5b947c0b3701769e991eaf1
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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