3-cyclopropyl-1H-pyrazol-5-amine → 2-Chloro-6-(2-chlorophenyl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-4-pyrimidinamine

HRID 855658Notes

Reaction equation

HRID 855658 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[N:3]=1.[CH:16]1([C:19]2[NH:23][N:22]=[C:21]([NH2:24])[CH:20]=2)[CH2:18][CH2:17]1>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:24][C:21]2[CH:20]=[C:19]([CH:16]3[CH2:18][CH2:17]3)[NH:23][N:22]=2)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[N:3]=1

Participants

4

Reactant 2

HCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 57498047HCID 57498047, compound

Product 1

HCID 589358582-Chloro-6-(2-chlorophenyl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-4-pyrimidinamineYield 38.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dichloro-6-(2-chloro-phenyl)-pyrimidine (180 mg, 0.694 mmol) and 5-cyclopropyl-1H-pyrazol-3-ylamine (128 mg, 1.04 mmol) was taken into 3 ml of ethanol. The reaction was stirred at room temperature for 4 days. The reaction was evaporated in vacuo and the crude product purified by flash chromatography (SiO2) eluting with ethyl acetate/hexane (1:1) to afford 93 mg of the desired product. HPLC (C18 column) Rt 6.23 mins.; MS m/z 346.1 (M+H) 344.1 (M−H)

Workup

  1. customThe reaction was evaporated in vacuo
  2. customthe crude product purified by flash chromatography (SiO2)
  3. washeluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-5b0ca75bde2f4d569f941361e920ff6e
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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