Triethylamine → 6-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

HRID 1946664

Reaction equation

HRID 1946664 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1.C(N(CC)CC)C.[Cl:17][C:18]1[N:23]=[CH:22][N:21]=[C:20]([C:24](Cl)=[O:25])[CH:19]=1.ClC1N=CN=C(C(NC2C=CC(O)=CC=2)=O)C=1>ClCCl>[Cl:17][C:18]1[N:23]=[CH:22][N:21]=[C:20]([C:24]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=2[CH3:9])=[O:25])[CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 178194-Amino-m-cresolHCID 184220986-Chloropyrimidine-4-carbonyl chlorideHCID 594468766-chloro-N-(4-hydroxyphenyl)pyrimidine-4-carboxamide

Product 1

HCID 594471056-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) solution of 4-amino-m-cresol (Fluka, 4.17 g, 33.9 mmol) and triethylamine (23.6 mL, 0.170 mol) in dry dichloromethane (100 mL) was treated with 6-chloropyrimidine-4-carbonyl chloride, obtained as described above for Intermediate 7, step 1 (6.0 g, 34 mmol) and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, diluted with water and extracted with EtOAc. The combined organic layers were dried on magnesium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (silica) using as eluent petroleum ether/EtOAc to afford the title compound as yellow solid.

Workup

  1. customobtained
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. customThe combined organic layers were dried on magnesium sulfate
  6. customevaporated in vacuo
  7. customThe crude product was purified by column chromatography (silica)

Sources & evidence

ORD record
ord-293e601e98894baca4aea202277ee4ff
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Linked notes

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