Dimethylamine → HCID 23381129, compound

HRID 1280567Notes

Reaction equation

HRID 1280567 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[C:13]2[N:15]([CH2:27][C:28]([OH:30])=O)[C:16](=[O:26])[N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[CH2:18][C:12]2=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)[N:49]2[CH2:53]CC[CH2:50]2)C2C=CC=CC=2N=N1.CNC>CN(C)C=O>[CH2:1]([S:8][C:9]1[N:14]=[C:13]2[N:15]([CH2:27][C:28]([N:49]([CH3:53])[CH3:50])=[O:30])[C:16](=[O:26])[N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[CH2:18][C:12]2=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 2724699PyBOPHCID 18425486HCID 18425486, compound

Product 1

HCID 23381129HCID 23381129, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-benzylthio-3-(2-chlorophenyl)-1-(hydroxycarbonylmethyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (500 mg, 1.13 mmol) and benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate) (885 mg, 1.70 mmol) in N,N-dimethylformamide (15 mL) was bubbled dimethylamine gas into the solution for two minutes, then stirred in a sealed tube for 2 hours. The reaction mixture was quenched with water and extracted into ethyl acetate. The combined organic extracts were washed with water, dried, filtered, concentrated in vacuo, and the residue was purified by column chromatography on silica gel using 36:1 dicloromethane/methanol as eluant. The column fractions containing product were combined and concentrated in vacuo to give 490 mg of 7-benzylthio-3-(2-chlorophenyl)-1-(dimethylaminocarbonyl-methyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted into ethyl acetate
  3. washThe combined organic extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by column chromatography on silica gel using 36:1 dicloromethane/methanol as eluant
  8. additionThe column fractions containing product
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50a3a01a0ecf4210b030a9e3ab4031ad
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

Loading…