Cyclopropylamine → [6-(2-Chloro-imidazol-1-yl)-pyrimidin-4-yl]-cyclopropyl-amine

HRID 19500Notes

Reaction equation

HRID 19500 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[Cl:13])[N:5]=[CH:4][N:3]=1.[CH:14]1([NH2:17])[CH2:16][CH2:15]1>CO>[Cl:13][C:9]1[N:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:17][CH:14]3[CH2:16][CH2:15]3)[CH:7]=2)[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 589730674-Chloro-6-(2-chloro-imidazol-1-yl)-pyrimidine

Product 1

HCID 58973138[6-(2-Chloro-imidazol-1-yl)-pyrimidin-4-yl]-cyclopropyl-amineYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

4-Chloro-6-(2-chloro-imidazol-1-yl)-pyrimidine (0.85 g, 4 mmol) and cyclopropylamine (1.4 mL, 20 mmol) were mixed in 10 mL methanol and stirred at 50° C. for 12 hours. After reaction was complete, the solvent was removed by rotary evaporation. The crude product was washed with water and taken to dryness to give the title compound (0.84 g, 90%); 1H NMR 400 MHz (DMSO-d6) δ 8.45 (s, 1H), 8.17 (d, 1H), 7.75 (s, 1 H), 7.08 (s, 1H), 6.80 (d, 1H), 3.34 (s, 1H), 0.78 (br, 2H), 0.52 (br, 2H); MS m/z 236.4 (M+1).

Workup

  1. customAfter reaction
  2. customthe solvent was removed by rotary evaporation
  3. washThe crude product was washed with water

Sources & evidence

ORD record
ord-7639acae788645ac9f0a1c2194593ae7
Source dataset
uspto-grants-2010_06
Patent number
US07745437B2

Reaction notes

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