Ammonia → 6-(2-Chloro-benzoimidazol-1-yl)-pyrimidin-4-ylamine

HRID 1968418Notes

Reaction equation

HRID 1968418 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11](Cl)[N:10]=[CH:9][N:8]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N:3]=1.[NH3:18]>CC(O)C>[Cl:1][C:2]1[N:6]([C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH2:18])[CH:12]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 598224532-Chloro-1-(6-chloropyrimidin-4-yl)-1H-benzimidazole

Product 1

HCID 598224556-(2-Chloro-benzoimidazol-1-yl)-pyrimidin-4-ylamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-Chloro-1-(6-chloro-pyrimidin-4-yl)-1H-benzoimidazole (500 mg, 1.89 mmol) and 10 mL 2 M Ammonia in 2-propanol is heated at 50° C. in a sealed tube for overnight. The reaction mixture is then cooled to room temperature, concentrated and treated with 10 mL H2O. The solid is collected by filtration and washed with water, dried to afford the title compound as a solid: 1H NMR 400 MHz (DMSO-d6) δ 8.50 (s, 1H), 7.72-7.67 (m, 1H), 7.60-7.55 (m, 1H), 7.44 (s, 2H), 7.37-7.31 (m, 2H), 6.71 (dd, J=1.2 Hz, 1H); MS m/z 246.1 (M+1).

Workup

  1. temperatureThe reaction mixture is then cooled to room temperature
  2. concentrationconcentrated
  3. additiontreated with 10 mL H2O
  4. filtrationThe solid is collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ce7c115d59364da58cd817432fa1063d
Source dataset
uspto-grants-2013_04
Patent number
US08426404B2

Reaction notes

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