Dichloromethane → HCID 18473275, compound

HRID 2227248Notes

Reaction equation

HRID 2227248 reaction equation
O[C:2]1[C:3]2[CH:11]=[CH:10][N:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:25][C:26]1[CH:34]=[C:33]2[C:29]([CH2:30][CH2:31][NH:32]2)=[CH:28][CH:27]=1.C(Cl)Cl>N1C=CC=CC=1.CN(C=O)C>[Cl:25][C:26]1[CH:34]=[C:33]2[C:29]([CH2:30][CH2:31][N:32]2[C:2]2[C:3]3[CH:11]=[CH:10][N:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 9845Trifluoroacetic anhydrideHCID 2585676-Chloro-2,3-dihydro-1h-indoleHCID 1785180321H-pyrido[3,4-d]pyrimidin-4-one

Product 1

HCID 18473275HCID 18473275, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-hydroxy-pyrido[3,4-d]pyrimidine (0.103 g, 0.70 mmol) in dry pyridine (2 ml) cooled in an ice-water bath was added dropwise trifluoroacetic anhydride (0.20 ml, 1.4 mmol). After stirring for 0.5 hour, 6-chloroindoline (0.10 g, 0.66 mmol) and pyridine (0.14 g, 1.81 mmol) in dry DMF (1.5 ml) was added dropwise. The cold bath was allowed to warm to ambient temperature and then heated at 70° C. for 3 hours. The reaction was cooled to ambient temperature and then added to methylene chloride (150 mL). The organic layer was washed with saturated sodium carbonate and water, and then dried over sodium sulfate. The solvent was removed by rotary evaporation and the residue purified by column chromatography (silica gel, 9/2/1-CH2Cl2/hexanes/methanol) to give a pale yellow residue (0.048 g, 28%): MP: 194-6° C.; LC/MS: 283 (MH+).

Workup

  1. temperaturecooled in an ice-water bath
  2. temperatureheated at 70° C. for 3 hours
  3. temperatureThe reaction was cooled to ambient temperature
  4. washThe organic layer was washed with saturated sodium carbonate and water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed by rotary evaporation
  7. customthe residue purified by column chromatography (silica gel, 9/2/1-CH2Cl2/hexanes/methanol)

Sources & evidence

ORD record
ord-8546e0e4d1474dcd84bd33d8d9e4fd90
Source dataset
uspto-grants-2002_07
Patent number
US06413971B1

Reaction notes

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