Dimethylformamide → HCID 58574671, compound

HRID 1619303Notes

Reaction equation

HRID 1619303 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[N:7]([CH3:14])[C:8]([CH2:12]Cl)=[N:9]2)=[CH:4][CH:3]=1.[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[N:7]([CH3:14])[C:8]([CH2:12][N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 58574686HCID 58574686, compound

Product 1

HCID 58574671HCID 58574671, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 7-bromo-2-(chloromethyl)-3-methylquinazolin-4(3H)-one (125 mg, 0.43 mmol), pyrrolidine (65 mg, 0.91 mmol), K2CO3 (244 mg, 1.768 mmol) and DMF (10 mL) was stirred at room temperature for 30 min. Then water was added and the mixture was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (3×10 mL), dried over Na2SO4, filtered and evaporated to give 100 mg of the desired product. MS (ESI): 322, 324 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layers were washed with brine (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0a4327f092974757a635f94f05e3c673
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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