Dimethylformamide → HCID 21936033, compound

HRID 1372998Notes

Reaction equation

HRID 1372998 reaction equation
[C:1]([O:4][CH:5]([CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=O)[NH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:19][CH3:20])(=[O:3])[CH3:2].CN(C=O)C.S(Cl)([Cl:34])=O>>[Cl:34][C:12]1[C:11]2[C:16](=[CH:17][C:8]([O:7][CH2:6][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[C:9]([O:19][CH3:20])[CH:10]=2)[N:15]=[CH:14][N:13]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 135763125HCID 135763125, compound

Product 1

HCID 21936033HCID 21936033, compound

Procedure

7-(2-Acetoxy-3-(pyrrolidin-1-yl)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (4.7 g) was suspended in thionyl chloride (55 ml), DMF (0.5 ml) was added and the mixture heated at reflex for 1 hour. The thionyl chloride was evaporated under vacuum, toluene was added and the solvent was evaporated. This process was repeated twice. The residue was taken up in ice/water, the pH adjusted to 7.5 with a saturated solution of sodium bicarbonate followed by sodium hydroxide 2N until pH 9 and the aqueous solution extracted twice with dichloromethane. The combined extracts were washed with water and brine, dried over magnesium sulphate and filtered. The filtrate was evaporated under vacuum and the residue triturated with ether to give 4-chloro-7-[2-acetoxy-3-(pyrrolidin-1-yl)propoxy]-6-methoxyquinazoline (4.1 g) as a white foam.

Workup

  1. temperaturethe mixture heated at reflex for 1 hour
  2. customThe thionyl chloride was evaporated under vacuum, toluene
  3. additionwas added
  4. customthe solvent was evaporated
  5. extractionthe aqueous solution extracted twice with dichloromethane
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customThe filtrate was evaporated under vacuum
  10. customthe residue triturated with ether

Sources & evidence

ORD record
ord-ba85493b4bf44b1f895f7dfed9fdedb5
Source dataset
uspto-grants-2007_01
Patent number
US07160889B2

Reaction notes

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