Dimethylformamide → 4-Chloro-7-methyl-2-oxo-1,5-diphenyl-1,2,5,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 470158Notes

Reaction equation

HRID 470158 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:8]2[C:13](=O)[NH:12][C:11](=[O:15])[N:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[NH:22][C:23]=1[CH3:24])=[O:5])[CH3:2].CN(C)C=O.O=P(Cl)(Cl)[Cl:38].C([O-])(=O)C.[K+]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:8]2[C:13]([Cl:38])=[N:12][C:11](=[O:15])[N:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[NH:22][C:23]=1[CH3:24])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517044Potassium AcetateHCID 498542117-Methyl-2,4-dioxo-1,5-diphenyl-1,2,3,4,5,8-hexahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 675148484-Chloro-7-methyl-2-oxo-1,5-diphenyl-1,2,5,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The compound from step 5 (11 g, 27.3 mmol) was taken in 100 ml dry chloroform and then charged with DMF (dimethylformamide) (2 ml, 27 mmol). POCl3 (14 ml) was dissolved in advance in 26 ml chloroform and was added under stirring in an argon atmosphere. The reaction mixture was then stirred at 70 C for 6 h. The reaction was monitored by LC-MS. The reaction mixture was cooled down to room temperature and poured into 25% ice cold solution of potassium acetate (150 ml) under vigorous stirring, organic phase was separated, aqueous phase was extracted with DCM (dichloromethane) (2×100 ml) and the combined organic solution was dried over magnesium sulfate and then the solvent was evaporated under vacuum yielding yellow solids (8.3 g, 19.7 mmol, 72%).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was then stirred at 70 C for 6 h
  3. customwas separated
  4. extractionaqueous phase was extracted with DCM (dichloromethane) (2×100 ml)
  5. dry with materialthe combined organic solution was dried over magnesium sulfate
  6. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-e70b5d5f28aa4a7ab616df66972fd0df
Source dataset
uspto-grants-2014_01
Patent number
US08629272B2

Reaction notes

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