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

HRID 2067733Notes

Reaction equation

HRID 2067733 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.[C:17]([O:25]CC)(=O)[CH2:18][C:19]([O:21]CC)=O.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:19]([OH:21])=[CH:18][C:17](=[O:25])[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

4

Reactant 3

HCID 7583Diphenyl EtherHCID 7761Diethyl MalonateHCID 598230553-Benzyl-6-(methylamino)pyrimidin-4(3H)-one2×

Product 1

HCID 598230373-Benzyl-5-hydroxy-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneYield 57%

Procedure

3-Benzyl-6-(methylamino)pyrimidin-4(3H)-one (compound 5A) (2 g, 9.3 mmol, 1 eq) and diethyl malonate (2 mL, 14.5 mmol, 1.55 eq) were heated in phenyl ether (3 mL, 19 mmol, 2 eq) at 240° C. in a microwave reactor for 6 hours. Upon cooling a precipitate formed which was filtered and washed with ether to give 1.5 g of the title compound as a tan solid (57%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.51 (s, 3 H) 5.20 (s, 2 H) 5.72 (s, 1 H) 7.31 (br. s., 1 H) 7.38 (d, J=3.03 Hz, 4 H) 8.93 (s, 1 H) 11.61 (s, 1 H). [M+H] calc'd for C15H13N3O3, 284; found, 284.

Workup

  1. temperatureUpon cooling a precipitate
  2. customformed which
  3. filtrationwas filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-6b2bf68f2f1a4bf58b2ed1e78bfcc0ba
Source dataset
uspto-grants-2012_10
Patent number
US08293901B2

Reaction notes

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