4-Amino-6-chloropyrimidine → N-(4-Dimethylaminomethyl-3-trifluoromethyl-phenyl)-pyrimidine-4,6-diamine

HRID 1038726Notes

Reaction equation

HRID 1038726 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[C:12]([F:15])([F:14])[F:13])[CH3:3].Cl[C:17]1[N:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=1>>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:17]2[CH:18]=[C:19]([NH2:23])[N:20]=[CH:21][N:22]=2)=[CH:7][C:6]=1[C:12]([F:14])([F:13])[F:15])[CH3:1]

Participants

3

Reactant 2

HCID 2380124-Amino-6-chloropyrimidineHCID 57431457853297-25-3

Product 1

HCID 66669985N-(4-Dimethylaminomethyl-3-trifluoromethyl-phenyl)-pyrimidine-4,6-diamine

Conditions

Temperature
150 °C

Procedure

The title compound is prepared as described in Example 152A but using 4-dimethylaminomethyl-3-trifluoromethyl-phenylamine (218 mg, 1.46 mmol, 1 eq.), 6-chloro-pyrimidin-4-ylamine, and stirring the reaction mixture for 5 h at 150° C. The crude product is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 92:8) to afford the title compound as a white solid. ESI-MS: 312.1 [MH]+; tR=1.20 min (purity: 100%, gradient J); TLC: Rf=0.16 (DCM/MeOH+1% NH3aq, 92:8).

Workup

  1. customThe title compound is prepared
  2. customThe crude product is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 92:8)

Sources & evidence

ORD record
ord-c98e6f80d06e4aa495b5e84d1fd2752d
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

Loading…