Water → HCID 58994237, compound

HRID 12728Notes

Reaction equation

HRID 12728 reaction equation
Cl.[O:2]=[C:3]1[NH:8][C:7](=[O:9])[C:6]([C:10]2[C:11]([C:16]#[N:17])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][NH:4]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29].O>CN(C=O)C>[CH3:29][O:28][CH:27]([O:30][CH3:31])[CH2:26][CH2:25][N:4]1[CH:5]=[C:6]([C:10]2[C:11]([C:16]#[N:17])=[N:12][CH:13]=[CH:14][CH:15]=2)[C:7](=[O:9])[NH:8][C:3]1=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 686915923-(2,4-Dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-pyridine-2-carbonitrile hydrochloride

Product 1

HCID 58994237HCID 58994237, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-pyridine-2-carbonitrile hydrochloride (Prep103, 500 mg, 2 mmol), and K2CO3 (413 mg, 3 mmol) in DMF (7 ml) was stirred for one hour at room temperature. 3-Bromo-1,1dimethoxy-propane (402 mg, 2.2 mmol) was added and stirring continued for 48 hours. Water was added and the product was extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated to give 210 mg of a yellow oil (33% yield).

Workup

  1. stirringstirring
  2. waitcontinued for 48 hours
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-f4e4c63036ca423886f85ed817f3c080
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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