N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine → HCID 178433139, compound

HRID 63168Notes

Reaction equation

HRID 63168 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][C@H:27]([OH:30])[CH2:26][CH2:25]1>>[CH3:13][C:12]1[C:7]([NH:23][C@H:24]2[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]2)=[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 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamineHCID 178511715HCID 178511715, compound

Product 1

HCID 178433139HCID 178433139, compound

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 trans-4-aminocyclohexanol instead of cyclopentanamine. The crude material was purified by crystallization from ethanol to afford the titled compound as a hydrochloride salt as a white solid. 1H NMR (300 MHz, methanol-d4) δ ppm 1.18-1.26 (m, 2H), 1.32-1.44 (m, 2H), 1.67 (d, J=11.28 Hz, 2H), 1.80-1.99 (m, 5H), 2.33 (s, 3H), 3.45-3.55 (m, 1H), 3.75-3.83 (m, 1H), 4.72 (s, 2H), 7.33 (bs, 1H), 7.44 (d, J=7.79 Hz, 1H), 7.83 (t, J=7.12 Hz, 1H), 8.53 (d, J=4.30 Hz, 1H); MS (ESI) m/z 328.3 (M+1)+.

Workup

  1. customThe titled compound was synthesized
  2. customThe crude material was purified by crystallization from ethanol

Sources & evidence

ORD record
ord-a79f3016af76439999b292f9a53e14e1
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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