Ethyl orthoformate → 7-benzyl-1-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

HRID 275333Notes

Reaction equation

HRID 275333 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:19](OCC)(OCC)OCC>CN(C=O)C>[CH3:9][N:5]1[C:4](=[O:10])[C:3]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:19]=[N:1][C:2]=2[NH:7][C:6]1=[O:8]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 125005046-Amino-3-methyl-5-(phenylmethylamino)pyrimidine-2,4-dione

Product 1

HCID 111186677-benzyl-1-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To 6-amino-3-methyl-5-(phenylmethylamino)pyrimidine-2,4-dione (24.6 g=0.1 mol) in DMF (125 ml) at 60° C. add triethyl orthoformate (75 ml=0.45 mol). Heat to 110° C. for 5 hr, cool in ice, filter, and wash with methanol, then ether, to obtain the title compound, m.p. 268°-71° C.

Workup

  1. temperaturecool in ice
  2. filtrationfilter
  3. washwash with methanol

Sources & evidence

ORD record
ord-a1f1974372d84433be00f25b58dcdfbe
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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