Methanol → 4,7-Dioxo-2-(2-propoxyphenyl)-3,4,7,8-tetrahydropyrimido[4,5-d]pyrimidine

HRID 372996Notes

Reaction equation

HRID 372996 reaction equation
CS[C:3]1[N:8]=[C:7]2[N:9]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH2:22][CH3:23])[NH:11][C:12](=[O:13])[C:6]2=[CH:5][N:4]=1.C[OH:25].[H-].[Na+].O>CS(C)=O.C(O)(=O)C>[O:13]=[C:12]1[C:6]2[CH:5]=[N:4][C:3](=[O:25])[NH:8][C:7]=2[N:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH2:22][CH3:23])[NH:11]1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydrideHCID 1355223017-Methylthio-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Product 1

HCID 1356707644,7-Dioxo-2-(2-propoxyphenyl)-3,4,7,8-tetrahydropyrimido[4,5-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

7-Methylthio-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine (0.66 g) and methanol (0.26 g) were added to a stirring suspension of sodium hydride (0.38 g, 50% suspension in oil) in dry dimethylsulphoxide (15 ml). The mixture was stirred at ambient temperature for 1.5 hours and at 70°-80° C. for 18 hours. The cooled reaction mixture was poured into water (500 ml), then glacial acetic acid (0.46 ml) was added and the mixture was extracted with chloroform (20o ml and then 2×100 ml). The combined extracts were washed with water, dried (magnesium sulphate) and evaporated under reduced pressure to yield a solid which was washed successively with ether and 40°-60° petroleum ether and recrystallised from dimethylformamide: water to yield a crude product (0.18 g). This together with another sample (0.24 g) similarly prepared was eluted from a silica column with chloroform and 10% methanol in chloroform. The combined fractions containing product were evaporated under reduced pressure and the residue recrystallised from dimethylformamide dilute hydrochloric acid and then from dimethylformamide to yield the title compound, 0.15 g, m.p. 271°-3° C. (decomposition).

Workup

  1. customThe cooled reaction mixture
  2. extractionthe mixture was extracted with chloroform (20o ml
  3. washThe combined extracts were washed with water
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated under reduced pressure
  6. customto yield a solid which
  7. washwas washed successively with ether and 40°-60° petroleum ether
  8. customrecrystallised from dimethylformamide
  9. customwater to yield a crude product (0.18 g)
  10. customThis together with another sample (0.24 g) similarly prepared
  11. washwas eluted from a silica column with chloroform and 10% methanol in chloroform
  12. additionThe combined fractions containing product
  13. customwere evaporated under reduced pressure
  14. customthe residue recrystallised from dimethylformamide dilute hydrochloric acid

Sources & evidence

ORD record
ord-df8d9dad79e7426486633eb5f86003e5
Source dataset
uspto-grants-1992_11
Patent number
US05162316

Reaction notes

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