Ammonia → HCID 86653273, compound

HRID 536412Notes

Reaction equation

HRID 536412 reaction equation
[Cl:1][C:2]1[C:3]([NH:24][C:25]2[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]3[CH2:21][CH2:20][NH:19][CH:18]([CH3:22])[CH2:17]3)=[CH:11][C:10]=2[F:23])=[N:6][CH:7]=1.N>C(Cl)Cl.CO>[Cl:1][C:2]1[C:3]([NH:24][C:25]2[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([C@@H:16]3[CH2:21][CH2:20][NH:19][C@@H:18]([CH3:22])[CH2:17]3)=[CH:11][C:10]=2[F:23])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58255015HCID 58255015, compound

Product 1

HCID 86653273HCID 86653273, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-Chloro-N2-(2-fluoro-5-methyl-4-(2-methylpiperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (20 mg, 0.046 mmol) was dissolved in a solvent mixture of DCM and methanol (0.5 mL, 10/1 v/v+0.175N NH3). The mixture was applied to preparative TLC in order to separate the cis and trans stereoisomers (eluent: 6% MeOH in DCM with 0.1N NH3) of 5-Chloro-N2-(2-fluoro-5-methyl-4-(2-methylpiperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as white solids. The trans isomer was the preparative TLC top band and the cis isomer was the preparative TLC bottom band; ESMS m/z 430.1 (M+H+); cis stereoisomer 1H NMR (400 MHz, MeOD-d4): δ 8.03 (s, 1H), 7.84 (d, 1H), 7.02 (d, 1H), 6.24 (d, 1H), 3.90-3.85 (m, 1H), 2.32 (s, 3H), 2.27 (s, 3H), 2.03-1.84 (m, 2H), 1.65-1.54 (m, 1H), 1.55 (d, 3H), 1.38-1.19 (m, 4H).

Workup

  1. customto separate the cis and trans stereoisomers (eluent: 6% MeOH in DCM with 0.1N NH3) of 5-Chloro-N2-(2-fluoro-5-methyl-4-(2-methylpiperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as white solids

Sources & evidence

ORD record
ord-70830c22100c4191b227d2a910539285
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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