4-Methoxybenzylamine → HCID 22125137, compound

HRID 1858254Notes

Reaction equation

HRID 1858254 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13](S(C)(=O)=O)=[N:14][CH:15]=2)[N:10]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][OH:30])[CH:23]=2)[C:9]1=[O:31].COC1C=CC(C[NH2:39])=CC=1>>[NH2:39][C:13]1[N:12]=[C:11]2[N:10]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][OH:30])[CH:23]=3)[C:9](=[O:31])[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Br:1])[CH2:17][C:16]2=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 754524-MethoxybenzylamineHCID 22124978HCID 22124978, compound

Product 1

HCID 22125137HCID 22125137, compoundYield 40%

Conditions

Temperature
100 °C

Procedure

A mixture of 300 mg (0.6 mmol) of 3-(2-bromophenyl)-7-methanesulfonyl -3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one and 1.5 ml of 4-methoxybenzylamine was heated at 100° C. for 1 hour. The mixture was cooled and partitioned between 30 ml of dichloromethane and 30 ml of 2M aqueous hydrochloric acid. The organic phase was dried over magnesium sulfate, filtered and evaporated. The residue was dissolved in 10 ml of trifluoroacetic acid and then heated at reflux for 3 hours. The mixture was cooled and evaporated and the residue was partitioned between 25 ml of ethyl acetate and 25 ml of saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and evaporated and the residue was subjected to column chromatography on silica gel using ethyl acetate for the elution. Product-containing fractions were combined and evaporated to give 105 mg (40%) of 7-amino-3-(2-bromophenyl)-3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 154° C.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between 30 ml of dichloromethane and 30 ml of 2M aqueous hydrochloric acid
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was dissolved in 10 ml of trifluoroacetic acid
  7. temperatureheated
  8. temperatureat reflux for 3 hours
  9. temperatureThe mixture was cooled
  10. customevaporated
  11. customthe residue was partitioned between 25 ml of ethyl acetate and 25 ml of saturated sodium bicarbonate solution
  12. dry with materialThe organic phase was dried over magnesium sulfate
  13. filtrationfiltered
  14. customevaporated
  15. washfor the elution
  16. customevaporated

Sources & evidence

ORD record
ord-6d6af105e0bd488cba36edbb252e4b1f
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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