Water → 2-Chloro-4-[(4-methylphenyl)amino]-5-pyrimidinecarboxamide

HRID 1260394Notes

Reaction equation

HRID 1260394 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[N:15]=[C:14](Cl)[C:13]([C:17]([NH2:19])=[O:18])=[CH:12][N:11]=1.C(N(CC)CC)C.O>CN(C=O)C>[Cl:9][C:10]1[N:15]=[C:14]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)[C:13]([C:17]([NH2:19])=[O:18])=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7813p-ToluidineHCID 8471TriethylamineHCID 212230802,4-Dichloropyrimidine-5-carboxamide

Product 1

HCID 585068162-Chloro-4-[(4-methylphenyl)amino]-5-pyrimidinecarboxamideYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of p-toluidine (46.9 g) in DMF (100 ml) was added dropwise to a solution of 2,4-dichloro-5-pyrimidinecarboxamide (80 g) and triethylamine (63.9 ml) in DMF (300 ml) with ice cooling. The mixture was stirred for 2 h allowing to warm to room temperature, then added to water (1 l) and stirred for 20 min. The slurry was filtered and the solid washed with water. The solid was suspended in a mixture of methanol (500 ml) and ether (500 ml), stirred for 20 min and filtered to give 2-chloro-4-[(4-methylphenyl)amino]-5-pyrimidinecarboxamide as pale yellow solid (94.2 g).

Workup

  1. stirringstirred for 20 min
  2. filtrationThe slurry was filtered
  3. washthe solid washed with water
  4. additionThe solid was suspended in a mixture of methanol (500 ml) and ether (500 ml)
  5. stirringstirred for 20 min
  6. filtrationfiltered

Sources & evidence

ORD record
ord-cc53bfdf19dd4c95a0495388805714e5
Source dataset
uspto-grants-2013_06
Patent number
US08470835B2

Reaction notes

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