Water → 6-Amino-1-isobutyl-5-methylamino-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

HRID 883546Notes

Reaction equation

HRID 883546 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6](=[S:12])[NH:5][C:4](=[O:13])[C:3]=1[NH:14][CH:15]=O.CSC.O>O1CCCC1.B.Cl>[NH2:1][C:2]1[N:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6](=[S:12])[NH:5][C:4](=[O:13])[C:3]=1[NH:14][CH3:15]

Participants

7

Reactant 3

HCID 962WaterHCID 1068Dimethyl SulfideHCID 86601051N-(6-Amino-1-isobutyl-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-formamide

Product 1

HCID 866010526-Amino-1-isobutyl-5-methylamino-2-thioxo-2,3-dihydro-1H-pyrimidin-4-oneYield 54%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 6331BoraneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

N-(6-Amino-1-isobutyl-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-formamide (0.25 g, 1.0 mmol) was suspended in dry tetrahydrofuran (5 mL) and borane.dimethylsulphide complex (1M in dichloromethane, 2.5 mL, 2.5 mmol) was added dropwise. The reaction mixture was stirred at ambient temperature for 2.5 h. To the resulting clear yellow solution was added a few drops of 2M hydrochloric acid to eliminate unreacted borane. Water was added and the resulting aqueous solution was extracted with dichloromethane (3×15 mL). The combined organic phase was washed with brine and dried over Na2SO4. The solvent was evaporated off under reduced pressure yielding the title compound (0.12 g, 54% yield). This material was used without further purification.

Workup

  1. extractionthe resulting aqueous solution was extracted with dichloromethane (3×15 mL)
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-b48fd937bc594fbaa42459bc24926b47
Source dataset
uspto-grants-2012_08
Patent number
US08236951B2

Reaction notes

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