3-Thiophenamine, tetrahydro-, 1,1-dioxide → N4-(1,1-dioxidotetrahydrothiophen-3-yl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

HRID 63160Notes

Reaction equation

HRID 63160 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]C[CH2:2]1.[O:23]=[S:24]1(=[O:30])CCC(N)C1>>[O:23]=[S:24]1(=[O:30])[CH2:4][CH2:5][CH: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)[CH2:2]1

Participants

3

Reactant 2

HCID 228073-Thiophenamine, tetrahydro-, 1,1-dioxideHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Product 1

HCID 71738798N4-(1,1-dioxidotetrahydrothiophen-3-yl)-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 (1,1-dioxidotetrahydro-3-thienyl)amine 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, CDCl3) δ ppm 1.91 (s, 3H), 2.22 (m, 1H), 2.29 (s, 3H), 2.20-2.26 (m, 1H), 2.80-2.91 (m, 1H), 2.95 (bs, 1H), 3.05-3.15 (m, 1H), 3.18-3.24 (m, 1H), 4.69 (bs, 2H), 4.80-4.89 (m, 2H), 5.92 (bs, 1H), 7.17 (t, J=3.9 Hz, 1H), 7.34 (d, J=5.8 Hz, 1H), 7.64 (t, J=6.4 Hz, 1H), 8.57 (d, J=2.8 Hz, 1H); MS (ESI) m/z 348.8 (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-48f1a5e040474969aafb58b7ee2514ac
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Reaction notes

Loading…