3,4-Difluoroaniline → 2-chloro-N4-(3,4-difluorophenyl)-5-fluoro-4-pyrimidineamine

HRID 2277807Notes

Reaction equation

HRID 2277807 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[F:18])[NH2:14]>>[Cl:1][C:2]1[N:7]=[C:6]([NH:14][C:13]2[CH:15]=[CH:16][C:17]([F:18])=[C:11]([F:10])[CH:12]=2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 774693,4-DifluoroanilineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 220610492-chloro-N4-(3,4-difluorophenyl)-5-fluoro-4-pyrimidineamine

Procedure

In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3,4-difluoroaniline gave 2-chloro-N4-(3,4-difluorophenyl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.10 (d, 1H, J=2.1 Hz), 7.72 (m, 1H), 7.22 (m, 2H), 6.95 (bs, 1H); LCMS: purity: 93%; MS (m/e): 260 (M+).

Workup

  1. customIn like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine

Sources & evidence

ORD record
ord-08cf2f2032524f8e90bc3a400bc4d951
Source dataset
uspto-grants-2015_09
Patent number
US09133133B2

Reaction notes

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