Diphenyl Ether → 3-Benzyl-5-hydroxy-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 1260436Notes

Reaction equation

HRID 1260436 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[C:11]([NH:15][CH3:16])[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][CH:18]([C:24]([O:26]CC)=O)[C:19]([O:21]CC)=O.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:24]([OH:26])=[C:18]([CH3:17])[C:19](=[O:21])[N:15]([CH3:16])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 11857Diethyl methylmalonateHCID 598230553-Benzyl-6-(methylamino)pyrimidin-4(3H)-one2×

Product 1

HCID 598230503-Benzyl-5-hydroxy-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Benzyl-6-(methylamino)pyrimidin-4(3H)-one (compound 5A) (10 g, 46.5 mmol, 1 eq) and diethyl methylmalonate (16 mL, 93 mmol, 2 eq) were heated in phenyl ether (20 mL, 127 mmol) at 240° C. for 3 hours. The solution was cooled and diethyl ether (100 mL) was added. A precipitate formed which was filtered and washed with ether to give 10.5 g of the title compound as a tan solid (76%). [M+H] calc'd for C16H15N3O3, 298. found, 298.

Workup

  1. temperatureThe solution was cooled
  2. customA precipitate formed which
  3. filtrationwas filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-299fcf29022e430399bc1bfff3ad5127
Source dataset
uspto-grants-2013_06
Patent number
US08470837B2

Reaction notes

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