Triethylamine → 2,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine

HRID 1641400Notes

Reaction equation

HRID 1641400 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:15]=[C:14]([CH:16]2[CH2:18][CH2:17]2)[NH:13][N:12]=1.C(N(CC)CC)C>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[NH:13][N:12]=2)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 595867992,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amineYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,4,5-trichloropyrimidine (533 mg, 2.93 mmol), 3-amino-5-cyclopropyl-1H-pyrazole (360 mg, 2.93 mmol) and triethylamine (0.49 ml) in EtOH (5 ml) was stirred at room temperature for 10 hours. Solvent was removed and EtOAc was added. The solution was washed with water and dried over anhydrous sodium sulfate and was concentrated to give title compound as a white solid (546 mg, 69%). The compound was carried to the next step without further purification. 1H NMR δ 0.92 (m, 2H), 1.20 (m, 2H), 2.18 (m, 1H), 6.40 (s, 1H), 8.60 (s, 1H), 9.90 (s, 1H), 12.60 (s, 1H).

Workup

  1. customSolvent was removed
  2. additionEtOAc was added
  3. washThe solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-68d0b90c92f841ffa95bc83105934bf0
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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