Dimethylformamide → 6-bromo-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde

HRID 1924216Notes

Reaction equation

HRID 1924216 reaction equation
O=P(Cl)(Cl)Cl.[Br:6][C:7]1[CH:8]=[N:9][C:10]2[N:11]([N:13]=[C:14]([CH3:16])[CH:15]=2)[CH:12]=1.CN([CH:20]=[O:21])C>>[Br:6][C:7]1[CH:8]=[N:9][C:10]2[N:11]([N:13]=[C:14]([CH3:16])[C:15]=2[CH:20]=[O:21])[CH:12]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 159800416-Bromo-2-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 170961496-bromo-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehydeYield 59%

Conditions

Temperature
0 °C

Procedure

POCl3 (1.84 mmol, 1.3 eq, 172 μl) is added dropwise to DMF (1 ml) at 0° C. and the resulting solution is stirred at 0° C. during 30 minutes. Then, a solution of 6-bromo-2-methylpyrazolo[1,5-a]pyrimidine x14 (1.415 mmol, 1 eq, 300 mg) in DMF (1 ml) is added and the mixture is stirred for 30 minutes at room temperature. The reaction is quenched with water (100 ml). The resulting solid is filtered and washed with water to give 200 mg of 6-bromo-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde x21 as a solid.

Workup

  1. stirringthe mixture is stirred for 30 minutes at room temperature
  2. customThe reaction is quenched with water (100 ml)
  3. filtrationThe resulting solid is filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-8eafdc9325aa4859b753beae8d4fbfc7
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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