Methylamine → HCID 135670774, compound

HRID 728022Notes

Reaction equation

HRID 728022 reaction equation
CS[C:3]1[N:4]=[N:5][C:6]2[C:12](=[O:13])[NH:11][C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH2:22][CH3:23])=[N:9][C:7]=2[N:8]=1.[CH3:24][NH2:25]>C(Cl)(Cl)Cl>[CH3:24][NH:25][C:3]1[N:4]=[N:5][C:6]2[C:12](=[O:13])[NH:11][C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH2:22][CH3:23])=[N:9][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 135670800HCID 135670800, compound

Product 1

HCID 135670774HCID 135670774, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Methylthio-8-oxo-6-(2-propoxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine (2.0 g) was treated with a solution of methylamine in industrial methylated spirit (33%, 30 ml) at 75° C. in a pressure vessel for 20 hours. The cooled reaction mixture was evaporated under reduced pressure to afford an oily solid which was dissolved in chloroform. The organic solution was washed with water, dried and evaporated under reduced pressure to afford a yellow oily solid which was eluted from a silica column with chloroform/methanol (5%). The fractions containing product were combined and evaporated under reduced pressure to afford a yellow solid (180 mg) which together with another sample (50 mg), similarly prepared, was recrystallised from ethanol to afford the title compound, 140 mg, m.p. 261°-263° C.

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated under reduced pressure
  3. customto afford an oily solid which
  4. washThe organic solution was washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customto afford a yellow oily solid which
  8. washwas eluted from a silica column with chloroform/methanol (5%)
  9. additionThe fractions containing product
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5aaa0e7bacae4dd7af1c8d53a800c65c
Source dataset
uspto-grants-1991_09
Patent number
US05047404

Reaction notes

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