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

HRID 415437Notes

Reaction equation

HRID 415437 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH3:10][C:11]1[NH:15][N:14]=[C:13]([NH2:16])[CH:12]=1.C(N(CC)CC)C>CCO>[Br:1][C:2]1[C:3]([NH:16][C:13]2[CH:12]=[C:11]([CH3:10])[NH:15][N:14]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 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 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (1.29 g, 5.66 mmol) in EtOH (15 ml) at room temperature was added a solution of 5-methyl-1H-pyrazol-3-amine (549 mg, 5.66 mmol) in EtOH (3 ml) and triethylamine (628 mg, 6.22 mmol) and the reaction mixture was stirred at room temperature overnight. The suspension was filtered and washed with water and dried to give the desired product as a white solid (1.27 g, 78%). NMR (CDCl3) 2.24 (s, 3H), 6.24 (s, 1H), 8.41 (s, 1H), 9.29 (s, 1H), 12.32 (s, 1H).

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-e09809372bc849d8b68d28301c4a3ff6
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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