Sodium cyanoborohydride → 5-[3-(4-Methoxyphenyl)propyl]barbituric acid

HRID 993052Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([CH:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[NH:15][C:14]2=[O:21])=O)=[CH:5][CH:4]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH:13]2[C:14](=[O:21])[NH:15][C:16](=[O:20])[NH:17][C:18]2=[O:19])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 10 g of 5-[3-(4-Methoxyphenyl)propionyl]barbituric Acid in 100 ml of acetic acid are added portionwise 4.5 g of sodium cyanoborohydride, then the mixture is heated to 60° C. After 1 hour the reaction mixture is cooled to room temperature and poured into ice. After 30 minutes a solid is recovered by filtration, which is dried under vacuum at 50° C. to give 8.74 g of the product, m.p. 195-197° C.

Workup

temperatureAfter 1 hour the reaction mixture is cooled to room temperature
additionpoured into ice
filtrationAfter 30 minutes a solid is recovered by filtration, which
customis dried under vacuum at 50° C.

Sources & evidence

ORD record: ord-2587492816d34123b56532bc57ad0fc3
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472396B1

Reaction notes

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