HCID 22125110, compound → HCID 9886452, compound

HRID 1858231Notes

Reaction equation

HRID 1858231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:19]CC3C=CC(OC)=CC=3)=[N:15][CH:16]=2)[N:11]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:10]1=[O:35]>FC(F)(F)C(O)=O>[NH2:19][C:14]1[N:13]=[C:12]2[N:11]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:10](=[O:35])[N:9]([C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH2:18][C:17]2=[CH:16][N:15]=1

Participants

3

Reactant 1

HCID 22125110HCID 22125110, compound

Product 1

HCID 9886452HCID 9886452, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 40 mg (0.96 mmol) of 3-(2,6-dichlorophenyl)-7-(4-methoxybenzyl)amino-3,4-dihydro-1-phenylpyrimido[4,5-d]pyrimidin-2(1H)-one in 5 ml of trifluoroacetic acid was heated at reflux for 5 hours. The mixture was evaporated and the residue was partitioned between 30 ml of ethyl acetate and 30 ml of 2M aqueous sodium hydroxide. The organic phase was dried over magnesium sulfate, filtered and evaporated and the residue was subjected to column chromatography on silica gel using dichloromethane/methanol (20:1) for the elution. Product-containing fractions were combined and evaporated to give 10 mg (27%) of 7-amino-3-(2,6-dichlorophenyl)-3,4-dihydro-1-phenylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point >300° C.

Workup

  1. temperatureat reflux for 5 hours
  2. customThe mixture was evaporated
  3. customthe residue was partitioned between 30 ml of ethyl acetate and 30 ml of 2M aqueous sodium hydroxide
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. washfor the elution
  8. customevaporated

Sources & evidence

ORD record
ord-670b73b831414fbc921c7c5d7de7716b
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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