4-Isopropylbenzylamine → N4-cyclohexyl-N2-(4-isopropylbenzyl)-5,6-dimethylpyrimidine-2,4-diamine

HRID 63102Notes

Reaction equation

HRID 63102 reaction equation
Cl.[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11](NCC3C=CC=CN=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:25]([C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1)([CH3:27])[CH3:26]>>[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH:33][CH2:32][C:31]3[CH:30]=[CH:29][C:28]([CH:25]([CH3:27])[CH3:26])=[CH:35][CH:34]=3)[N:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 1382214-IsopropylbenzylamineHCID 131737202N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine hydrochloride

Product 1

HCID 71738266N4-cyclohexyl-N2-(4-isopropylbenzyl)-5,6-dimethylpyrimidine-2,4-diamine

Procedure

The titled compound was synthesized according to the general procedure described for preparation of N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 1) using (4-isopropylbenzyl)amine instead of (pyridin-2-ylmethyl)amine. The product 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 1.08 (d, J=15.04 Hz, 1H), 1.17 (d, J=6.72 Hz, 6H), 1.24-1.31 (m, 4H), 1.60 (s, 1H), 1.68 (t, J=11.95 Hz, 4H), 1.87 (s, 3H), 2.22 (s, 3H), 2.84 (t, J=13.90, 6.88 Hz, 1H), 3.89 (d, J=7.52 Hz, 1H), 4.48 (d, J=5.37 Hz, 2H), 7.14-7.28 (m, 4H), 7.55 (d, J=7.52 Hz, 1H), 8.06 (s, 1H), 12.69 (bs, 1H); MS (ESI) m/z 353.0 (M+1)+.

Workup

  1. customThe titled compound was synthesized
  2. customThe product 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-1e3a999d0f254373a6e4c52be7195425
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

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