Ethanol → 3-bromo-6-methylpyrazolo[1,5-a]pyrimidine

HRID 1842598Notes

Reaction equation

HRID 1842598 reaction equation
[NH2:1][C:2]1[C:6]([Br:7])=[CH:5][NH:4][N:3]=1.CN(C)[CH:10]=[C:11]([CH3:14])[CH:12]=O.C(O)C>C(O)(=O)C>[Br:7][C:6]1[CH:5]=[N:4][N:3]2[CH:12]=[C:11]([CH3:14])[CH:10]=[N:1][C:2]=12

Participants

5

Reactant 3

HCID 702EthanolHCID 5658623-(Dimethylamino)-2-methyl-2-propenalHCID 178509245HCID 178509245, compound

Product 1

HCID 187323293-bromo-6-methylpyrazolo[1,5-a]pyrimidineYield 71.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Amino-4-bromopyrazole (0.331 g, 2.04 mmol) and 3-(dimethylamino)-2-methyl-2-propenal (0.220 g, 1.94 mmol) were dissolved in acetic acid (6.48 mL) and ethanol (9.72 mL) and the reaction stirred at room temperature for 16 h. Solvents were removed under reduced pressure. The remaining residue was taken up in dichloromethane and purified by column chromatography (20-80% EtOAc/Hex) to give the title compound (0.294 g, 1.39 mmol). LRMS (APCI) calc'd for (C7H6BrN3) [M+H]+, 212.0; found 211.9. 1H NMR (500 MHz, cdcl3) δ 8.44 (s, 2H), 8.04 (s, 1H), 2.40 (s, 3H).

Workup

  1. customSolvents were removed under reduced pressure
  2. custompurified by column chromatography (20-80% EtOAc/Hex)

Sources & evidence

ORD record
ord-893fb85d115a437388cc878cd50fddb3
Source dataset
uspto-grants-2015_02
Patent number
US08946237B2

Reaction notes

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