Ammonium Acetate → HCID 68061984, compound

HRID 2173835Notes

Reaction equation

HRID 2173835 reaction equation
[CH:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)=[N:13][CH:14]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:31].[Na+]>CO>[CH:1]1([CH:7]([C:9]2[CH:10]=[N:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)=[N:13][CH:14]=2)[NH2:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 67980730HCID 67980730, compound

Product 1

HCID 68061984HCID 68061984, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude cyclohexyl{2-[4-(trifluoromethyl)phenyl]pyrimidin-5-yl}methanone (505 mg, 1.51 mmol), and ammonium acetate (1.19 g, 15.1 mmol) in methanol (7.6 ml) was added sodium cyanoborohydride (0.150 g, 2.26 mmol). The flask was fitted with a reflux condenser and heated to reflux for 12 hours. The reaction was concentrated in vacuo, then diluted with dichloromethane and aqueous 1.0M sodium hydroxide. The mixture was stirred for 30 minutes, whereupon the aqueous layer was extracted with dichloromethane (3×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was diluted in dichloromethane, passed through a plug of SiO2 with 20% methanol in dichloromethane and was concentrated in vacuo. The crude product was used without further purification.

Workup

  1. customThe flask was fitted with a reflux condenser
  2. temperatureheated
  3. temperatureto reflux for 12 hours
  4. concentrationThe reaction was concentrated in vacuo
  5. additiondiluted with dichloromethane and aqueous 1.0M sodium hydroxide
  6. extractionwas extracted with dichloromethane (3×)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. additionThe crude material was diluted in dichloromethane
  11. concentrationwas concentrated in vacuo
  12. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-202c759d4a4742f29caecab00cc1454c
Source dataset
uspto-grants-2015_06
Patent number
US09056834B2

Reaction notes

Loading…