Diisopropylethylamine → 5-bromo-2-chloro-N-(5-methyl-1H-pyrazol-3-yl)-4-Pyrimidinamine

HRID 2111668Notes

Reaction equation

HRID 2111668 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][C:11]1[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=1.C(N(CC)C(C)C)(C)C>C(O)CCC>[Br:1][C:2]1[C:3]([NH:10][C:11]2[CH:15]=[C:14]([CH3:16])[NH:13][N:12]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 509936455-bromo-2-chloro-N-(5-methyl-1H-pyrazol-3-yl)-4-PyrimidinamineYield 85.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-bromo-2,4-dichloropyrimidine (10.0 g, 44 mmol), 3-amino-5-methyl-1H-pyrazole (6.0 g, 62 mmol) and N,N-diisopropylethylamine (9.20 ml, 53 mmol) in 1-butanol (80 ml) was heated at 85° C. for 12 hours. The mixture was allowed to cool to ambient temperature and the resulting precipitate collected by filtration. The solid product was washed with ethanol and dried to give the sub-titled compound (10.8 g, 85%). 1H NMR (DMSO): δ 2.23 (s, 3H), 6.23 (s, 1H), 8.39 (s, 1H), 9.21 (s, 1H), 12.27 (s, 1H); MS: m/z 290 (MH)+.

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. washThe solid product was washed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-d107a87eff914e16a666f2f870c5e581
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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