Ethanol → N4-Methyl-N6-[3-(trifluoromethyl)phenyl]-4,6-pyrimidinediamine

HRID 1038684Notes

Reaction equation

HRID 1038684 reaction equation
[CH3:1][NH2:2].C(O)C.Cl[C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[CH:8]=1>>[CH3:1][NH:2][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:10]=[CH:11][N:12]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 577809026-Chloro-N-[3-(trifluoromethyl)-phenyl]pyrimidin-4-amine

Product 1

HCID 66669958N4-Methyl-N6-[3-(trifluoromethyl)phenyl]-4,6-pyrimidinediamine

Conditions

Temperature
100 °C

Procedure

A solution of methylamine in ethanol (32 mL, 256 mmol) is added to (6-chloro-pyrimidin-4-yl)-(3-trifluoromethyl-phenyl)-amine (3.49 g, 12.8 mmol) and the mixture is stirred for 5 h at 100° C. in a pressure bottle. The reaction mixture is concentrated in vacuo, the residue diluted with CH3OH and basified using conc. aqueous ammonia solution. The product is filtered off, washed with H2O and CH3OH and dried in vacuo.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionthe residue diluted with CH3OH and basified using conc. aqueous ammonia solution
  3. filtrationThe product is filtered off
  4. washwashed with H2O and CH3OH
  5. customdried in vacuo

Sources & evidence

ORD record
ord-7b34c4adddf34c219fc10b5669b169a5
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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