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

HRID 63150

반응식

HRID 63150 반응식
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.[F:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[NH2:31]>>[F:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[NH:31][C:7]1[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[N:8]=1

참가 물질

3

반응물 2

HCID 677752,5-DifluoroanilineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

생성물 1

HCID 71738688N4-(2,5-difluorophenyl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

실험 절차

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 (2,5-difluorophenyl)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 light-yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 2.09 (s, 3H), 2.35 (s, 3H), 4.75 (d, J=4.8 Hz, 2H), 5.96 (bs, 1H), 6.656-6.62 (m, 1H), 6.67 (bs, 1H), 7.01 (m, 1H), 7.16 (t, J=5.4 Hz, 1H), 7.37 (d, J=7.8 Hz, 1H), 7.62 (t, J=7.8 Hz, 1H), 8.29 (bs, 1H), 8.59 (d, J=3.4 Hz, 1H); MS (ESI) m/z 342.7 (M+1)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a465f00518344d6ea3aa0f0a2d717434
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447051B2

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