2,4-Dichloro-5-fluoropyrimidine → HCID 22060779, compound

HRID 71295Notes

Reaction equation

HRID 71295 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[C:10]1([C:16]2[O:17][C:18]([C:21]3[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=3)[NH2:24])=[N:19][N:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[Cl:1][C:2]1[N:7]=[C:6]([NH:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:21]([C:18]3[O:17][C:16]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)=[N:20][N:19]=3)[CH:22]=2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 8183673-(5-Phenyl-1,3,4-oxadiazol-2-yl)aniline

Product 1

HCID 22060779HCID 22060779, compound

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-(2-phenyl-1,3,4-oxadiazol-5-yl)aniline gave 2-chloro-5-fluoro-N4-[3-(2-phenyl-1,3,4-oxadiazol-5-yl)phenyl)-4-pyrimidineamine. 1H NMR (DMSO-d6): δ 10.28 (s, 1H), 8.62 (s, 1H), 8.39 (d, 1H, J=3.3 Hz), 8.11 (m, 2H), 7.98 (bd, 1H, J=6.9 Hz), 7.88 (bd, 1H, J=8.4 Hz), 7.65 (m, 4H); LCMS: purity: 76%; MS (m/e): 76%.

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-e1daacd421764e4aa0ec5780017aeb48
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Reaction notes

Loading…