(1R,2S)-2-Aminocyclohexanemethanol → rac-[(1R,2S)-2-({5,6-dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4-yl}amino)cyclohexyl]methanol

HRID 63133Notes

Reaction equation

HRID 63133 reaction equation
C1(N[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:8]=2)CCCC1.[NH2:23][C@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[CH2:30][OH:31]>>[CH3:13][C:12]1[C:7]([NH:23][C@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]2[CH2:30][OH:31])=[N:8][C:9]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[N:10][C:11]=1[CH3:14]

Participants

3

Reactant 2

HCID 2724653(1R,2S)-2-AminocyclohexanemethanolHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Product 1

HCID 71738551rac-[(1R,2S)-2-({5,6-dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4-yl}amino)cyclohexyl]methanol

Procedure

The titled compound was synthesized according to the procedure described for preparation of N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 29) using rac-[(1R,2S)-2-aminocyclohexyl]methanol instead of cyclopentanamine. The crude material was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1), and then the final product was washed with diethyl ether to afford the titled compound as a white solid. 1H NMR (400 MHz, methanol-d6) δ ppm 1.35 (bs, 2H), 1.50 (bs, 6H), 1.89 (bs, 3H), 2.20 (bs, 3H), 3.40-3.48 (m, 1H), 3.60-3.68 (m, 1H), 4.10-4.18 (m, 1H), 4.64 (bs, 2H), 7.26 (t, J=5.64 Hz, 1H), 7.40 (d, J=8.06 Hz, 1H), 7.75 (d, J=7.79 Hz, 1H), 8.46 (d, J=4.83, 1H); MS (ESI) m/z 342.8 (M+1)+.

Workup

  1. customThe titled compound was synthesized
  2. customThe crude material was purified by column chromatography
  3. washeluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1)
  4. washthe final product was washed with diethyl ether

Sources & evidence

ORD record
ord-974b5b0974ce48079a153273b0c0585f
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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