7-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide → HCID 136174433, compound

HRID 2073211

Reaction equation

HRID 2073211 reaction equation
F[C:2](F)(F)[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[Na]>C(O)(=O)C>[CH3:2][C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 27776927-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamideHCID 5360545Sodium

Product 1

HCID 136174433HCID 136174433, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-[3-Methylphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamine (prepared as described in Example 1) is stirred as a suspension in gacial acetic acid (cooled in an ice bath) under nitrogen and then excess sodium cyanoborohydide is added to the reaction mixture in portions. After one hour of stirring in the ice bath, the mixture is stirred at room temperature for 19 hours. This solution is evaporated to dryness, then water is added and the white precipitate which forms is collected by filtration and washed with an aqueous saturated solution of sodium bicarbonate, and finally with water. The solid is collected by filteration and dried to give 4,5-dihydro-7-(3-methylphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide.

Workup

  1. customThis solution is evaporated to dryness
  2. additionwater is added
  3. filtrationthe white precipitate which forms is collected by filtration
  4. washwashed with an aqueous saturated solution of sodium bicarbonate
  5. customThe solid is collected by filteration
  6. customdried

Sources & evidence

ORD record
ord-13273e52e29d4e92b3d25db03243337d
Source dataset
uspto-grants-1990_04
Patent number
US04916137

Linked notes

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