Methane → HCID 135474375, compound

HRID 372989Notes

Reaction equation

HRID 372989 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.[CH:24]1([NH2:27])[CH2:26][CH2:25]1.C>C(O)C.[OH-].[Na+]>[CH:24]1([NH:27][C:3]2[N:8]=[C:7]3[N:9]=[C:10]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[O:20][CH2:21][CH2:22][CH3:23])[NH:11][C:12](=[O:13])[C:6]3=[CH:5][N:4]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 297MethaneHCID 69828Cyclopropylamine2×HCID 1355223017-Methylthio-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Product 1

HCID 135474375HCID 135474375, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 7-methylthio-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine (0.60 g) and cyclopropylamine (1.2 ml) in ethanol (20 ml) was heated for 18 hours at 90° C. in a pressure vessel. Further cyclopropylamine (1 ml) was added and the reaction mixture was stirred in a pressure vessel for 18 hours at 100° C. and then for 20 hours at 120° C. The cooled reaction mixture was evaporated under reduced pressure to yield a residue which was dissolved in 1 Normal sodium hydroxide. The resultant solution was treated with charcoal, filtered and the filtrate neutralised by the addition of concentrated hydrochloric acid which caused the precipitation of a crude product. The crude product was eluted from a silica column with chloroform as eluant, and the combined fractions containing product were evaporated under reduced pressure to yield a residue. This was twice recrystallised from methanol to yield the title compound, 0.23 g, m.p. 207.5°-208.5° C.

Workup

  1. waitfor 20 hours at 120° C
  2. customThe cooled reaction mixture
  3. customwas evaporated under reduced pressure
  4. customto yield a residue which
  5. filtrationfiltered
  6. additionthe filtrate neutralised by the addition of concentrated hydrochloric acid which
  7. customthe precipitation of a crude product
  8. washThe crude product was eluted from a silica column with chloroform as eluant
  9. additionthe combined fractions containing product
  10. customwere evaporated under reduced pressure
  11. customto yield a residue
  12. customThis was twice recrystallised from methanol

Sources & evidence

ORD record
ord-dab5301722c7456ebddf147f6bdae15b
Source dataset
uspto-grants-1992_11
Patent number
US05162316

Reaction notes

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