2-Amino-5-methylpyridine → (2S)-3-[2-(tert-butyl-dimethylsilyl)oxyethoxy]-2-[1-(3-fluoro-2-methylphenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxy-N-(5-methylpyridin-2-yl)propanamide

HRID 1098183Notes

Reaction equation

HRID 1098183 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][O:21][CH2:22][C@H:23]([O:28][C:29]1[N:34]=[CH:33][N:32]=[C:31]2[N:35]([C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=3[CH3:45])[N:36]=[CH:37][C:30]=12)[C:24]([O:26]C)=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1C=CC=CC=1)[C:2]1C=CC=CC=1.[CH3:46][C:47]1[CH:48]=[CH:49][C:50]([NH2:53])=[N:51][CH:52]=1>>[Si:1]([O:18][CH2:19][CH2:20][O:21][CH2:22][C@H:23]([O:28][C:29]1[C:30]2[CH:37]=[N:36][N:35]([C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:39]=3[CH3:45])[C:31]=2[N:32]=[CH:33][N:34]=1)[C:24]([NH:53][C:50]1[CH:49]=[CH:48][C:47]([CH3:46])=[CH:52][N:51]=1)=[O:26])([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:8])[CH3:2]

Participants

3

Reactant 2

HCID 153482-Amino-5-methylpyridineHCID 59279546(2S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(3-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate

Product 1

HCID 57504658(2S)-3-[2-(tert-butyl-dimethylsilyl)oxyethoxy]-2-[1-(3-fluoro-2-methylphenyl)pyrazolo[4,5-e]pyrimidin-4-yl]oxy-N-(5-methylpyridin-2-yl)propanamide

Procedure

Prepared using a procedure analogous to that described for Intermediate AE1 using (2S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(3-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate (Intermediate AF4) and 5-methylpyridin-2-amine. 1H NMR (400 MHz, DMSO) d 0.88 (9H, s), 1.96 (3H, d), 2.24 (3H, s), 3.75 (4H, m), 4.08-4.02 (1H, m), 4.14 (1H, m), 5.99 (1H, m), 7.50-7.29 (9H, m), 7.63-7.54 (5H, m), 7.89 (1H, d), 8.17 (1H, s), 8.51 (1H, s), 8.55 (1H, s), 10.94 (1H, s).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5d188e9c9d534a49a70f09e5289a8e84
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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