3-(1,3-Oxazol-5-yl)aniline → 5-fluoro-N4-(3-hydroxyphenyl)-N2-(3-(1,3-oxazol-5-yl)phenyl]-2,4-pyrimidinediamine

HRID 71590Notes

Reaction equation

HRID 71590 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[C:5]([F:16])=[CH:4][N:3]=1.[O:17]1[C:21]([C:22]2[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=2)[NH2:25])=[CH:20][N:19]=[CH:18]1>>[F:16][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)=[N:7][C:2]([NH:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:22]([C:21]3[O:17][CH:18]=[N:19][CH:20]=3)[CH:23]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 27392893-(1,3-Oxazol-5-yl)anilineHCID 220604512-chloro-5-fluoro-N-(3-hydroxyphenyl)-4-pyrimidineamine

Product 1

HCID 220606035-fluoro-N4-(3-hydroxyphenyl)-N2-(3-(1,3-oxazol-5-yl)phenyl]-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine, the reaction of 2-chloro-5-fluoro-N4-(3-hydroxyphenyl)-4-pyrimidineamine with 3-(1,3-oxazol-5-yl)aniline gave 5-fluoro-N4-(3-hydroxyphenyl)-N2-(3-(1,3-oxazol-5-yl)phenyl]-2,4-pyrimidinediamine. LCMS: purity: 76%; MS (m/e): 364 (MH+).

Workup

  1. customIn like manner to the preparation of N4-(3-chloro-4-trifluoromethoxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidineamine

Sources & evidence

ORD record
ord-45f87b9dcecd4fe6a1224e59c12e3ecd
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Reaction notes

Loading…