Cycloheptylamine → N4-cycloheptyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

HRID 63135Notes

Reaction equation

HRID 63135 reaction equation
[CH:1]1([NH:6][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)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:23]1(N)CCCCC[CH2:24]1>>[CH:1]1([NH:6][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)[CH2:5][CH2:4][CH2:3][CH2:2][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 2899CycloheptylamineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Product 1

HCID 71738553N4-cycloheptyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

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 1-cycloheptylamine 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 (300 MHz, DMSO-d6) δ ppm 1.26-1.32 (m, 2H), 1.38-1.50 (m, 8H), 1.68 (bs, 2H), 1.81 (s, 3H), 2.07 (s, 3H), 3.80-3.88 (m, 1H), 4.49 (d, J=9.91, 2H), 5.70 (d, J=7.25, H), 6.63 (brs, 1H), 7.15-7.20 (m, 1H), 7.21-7.28 (m, 1H), 7.68 (t, J=7.25, 1H), 8.46 (bs, 1H); MS (ESI) m/z 326.9 (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-7dc9f4e9cc2c4e92acbac9e916dc4caa
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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