HCID 3295594, compound → HCID 136078962, compound

HRID 1409284Notes

Reaction equation

HRID 1409284 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH:11]1[N:16]2[N:17]=[CH:18][N:19]=[C:15]2[NH:14][C:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[CH:12]1>CO.O>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[C@H:11]1[N:16]2[N:17]=[CH:18][N:19]=[C:15]2[NH:14][C@@H:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:12]1

Participants

5

Reactant 2

HCID 3295594HCID 3295594, compoundHCID 4311764Sodium borohydride

Product 1

HCID 136078962HCID 136078962, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (10 mmol) was added to a suspension of 7-(2-Chloro-6-fluorophenyl)-5-(4-chlorophenyl)-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidine (1 mmol) in methanol (5 mL). The reaction mixture was refluxed for 30 min, then cooled to room temperature, diluted with water (50 mL) and stirred sufficiently. The resulting mixture was filtered and washed with water to give the crude product, which was further purified by recrystallization from a mixture of EtOAc and Hexanes to provide the product as a white solid. Yield: 89%. m.p. 227-228° C. Rf=0.16 (EtOAc/Hexanes 33.3:66.7). MS: MH+=363. 1H NMR (500 MHz, DMSO-d6): δ 7.54-7.15 (m, 8H, CHar), 5.98-5.94 (m, 1H, CH), 4.82-4.78 (m, 1H, CH), 2.47-2.13 (m, 2H, CH2). HPLC: 99.8% (Method A, tR=3.67 min).

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. filtrationThe resulting mixture was filtered
  3. washwashed with water
  4. customto give the crude product, which
  5. customwas further purified by recrystallization from a mixture of EtOAc and Hexanes

Sources & evidence

ORD record
ord-e8caf66142524079ae356ea1ed929616
Source dataset
uspto-grants-2014_12
Patent number
US08921381B2

Reaction notes

Loading…