Diphenyl Ether → HCID 59823061, compound

HRID 1660872Notes

Reaction equation

HRID 1660872 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:9][CH3:10])[N:4]=[CH:3]1.[C:11]([O:19]CC)(=O)[CH2:12][C:13]([O:15]CC)=O.C1(OC2C=CC=CC=2)C=CC=CC=1.CN1CCCC1=O>>[OH:19][C:11]1[C:12]2[C:13](=[O:15])[N:9]([CH3:10])[CH:5]=[N:4][C:3]=2[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=1

Participants

5

Reactant 4

HCID 7583Diphenyl EtherHCID 7761Diethyl MalonateHCID 13387N-methyl-2-pyrrolidoneHCID 552881473-Methyl-6-(methylamino)-4(3H)-pyrimidinone2×

Product 1

HCID 59823061HCID 59823061, compound

Procedure

3-Methyl-6-(methylamino)pyrimidin-4(3H)-one (compound 1B; 400 mg, 2.88 mmol, 1 eq), diethyl malonate (873 μl, 5.76 mmol, 2 eq) and phenyl ether (915 μl, 5.76 mmol, 2 eq) were dissolved in 1-methyl-2-pyrrolidinone (2 ml, 20 mmol). The mixture was placed in a microwave reactor at 240° C. for 30 minutes to yield 5-hydroxy-3,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (compound 1C). The product was confirmed by LC-MS and isolated by HPLC to give 125 mg (21%) of compound 1C. [M+H] calc'd for C9H9N3O3, 208; found, 208.

Sources & evidence

ORD record
ord-ac515cc3c29044f5994bb69596b42049
Source dataset
uspto-grants-2011_10
Patent number
US08030317B2

Reaction notes

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