Water → HCID 22060618, compound

HRID 1960959Notes

Reaction equation

HRID 1960959 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[OH:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13].O>CO>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:10]([OH:9])[CH:11]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 115683-AminophenolHCID 709434,6-Dichloropyrimidine

Product 1

HCID 22060618HCID 22060618, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction of 4,6-dichloropyrimidine with excess 3-hydroxyaniline in MeOH at 80 0° C. for 24 h followed by dilution with water and acidification gave the crude product which was purified by silica gel column chromatography to obtain 6-chloro N4-(3-hydroxyphenyl)-4-pyrimidineamine. 1H NMR (CD3OD): δ 8.36 (d, 1H, J=1.2 Hz), 7.15 (t, 1H, J=8.4 Hz), 6.93 (dd, 1.2 and 8.1 Hz), 6.74 (d, 1H, J=1.2 Hz), 6.55 (dd, 1.8 and 8.1 Hz); LCMS (m/e): ret. time: 19.75 purity: 99%; MS (m/e): 222 (MH+).

Workup

  1. customgave the crude product which
  2. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f1db4d95cc7d41f18e56d0545394d33d
Source dataset
uspto-grants-2013_04
Patent number
US08410266B2

Reaction notes

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