7-Chloro-5-methylpyrazolo[1,5-a]pyrimidine → 7-[(3-Bromo-2-(2-cyanophenyl)benzofuran-5-yl)methylamino]-5-methylpyrazolo[1,5-a]pyrimidine

HRID 1450393Notes

Reaction equation

HRID 1450393 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH3:11])[CH:3]=1.[NH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]#[N:29])=[C:19]([Br:30])[C:18]=2[CH:31]=1>C(O)C>[Br:30][C:19]1[C:18]2[CH:31]=[C:14]([CH2:13][NH:12][C:2]3[N:7]4[N:8]=[CH:9][CH:10]=[C:6]4[N:5]=[C:4]([CH3:11])[CH:3]=3)[CH:15]=[CH:16][C:17]=2[O:21][C:20]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]#[N:29]

Participants

4

Reactant 2

HCID 104872877-Chloro-5-methylpyrazolo[1,5-a]pyrimidineHCID 199759705-(Aminomethyl)-3-bromo-2-(2-cyanophenyl)benzofuran

Product 1

HCID 199759617-[(3-Bromo-2-(2-cyanophenyl)benzofuran-5-yl)methylamino]-5-methylpyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.7 g (10.1 mmol) 7-chloro-5-methylpyrazolo[1,5-a]pyrimidine (prepared according to Y. Makisumi, Chem. Pharm. Bull. 1962, 10, 620) and 3.27 g (10.0 mmol) 5-(aminomethyl)-3-bromo-2-(2-cyanophenyl)benzofuran (prepared according to WO 92/09600) in 50 ml dry ethanol was heated with reflux for 5 h. The title compound precipitated upon cooling to room temperature, was filtered with suction, and recrystallized from ethanol to give colorless crystals. yield: 3.5 g (76%), m.p. 210°-215° C.

Workup

  1. temperaturewith reflux for 5 h
  2. customThe title compound precipitated
  3. filtrationwas filtered with suction
  4. customrecrystallized from ethanol
  5. customto give colorless crystals

Sources & evidence

ORD record
ord-7b9c4cce776d47f8a7ce17c3a898c3b9
Source dataset
uspto-grants-1997_02
Patent number
US05602137

Reaction notes

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