Dimethylformamide → 4-Chloro-7-methoxy-6-(3-(4-morpholinyl)propoxy)quinazoline

HRID 1803017Notes

Reaction equation

HRID 1803017 reaction equation
CN(C=O)C.Cl[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][N:15]=[C:14]2[Cl:23].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(Cl)Cl>O>[O:27]1[CH2:28][CH2:29][N:24]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][C:20]=2[O:21][CH3:22])[N:17]=[CH:16][N:15]=[C:14]3[Cl:23])[CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 8083MorpholineHCID 507422644-Chloro-6-(3-chloropropoxy)-7-methoxyquinazoline

Product 1

HCID 226492214-Chloro-7-methoxy-6-(3-(4-morpholinyl)propoxy)quinazolineYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DMF (3 lt), 6-(3-chloropropoxy)-7-methoxy-4-chloro quinazoline (200 gm) and morpholine (210 gm), were heated to 70-75° C. for 6-8 hours. The reaction mass was cooled to room temperature, and methylene chloride (2.5 lt) and water (2.5 lt) were charged. The layers separated and the aqueous layer extracted with methylene chloride twice (500 ml). The combined methylene chloride layer was washed with water, dried over sodium sulphate (10 gm) and concentrated completely at 35-40° C. to yield the title compound (200 gm, 85% yield).

Workup

  1. customThe layers separated
  2. extractionthe aqueous layer extracted with methylene chloride twice (500 ml)
  3. washThe combined methylene chloride layer was washed with water
  4. dry with materialdried over sodium sulphate (10 gm)
  5. concentrationconcentrated completely at 35-40° C.

Sources & evidence

ORD record
ord-fe7033e0683c4b5ab74d31380884b9c7
Source dataset
uspto-grants-2013_01
Patent number
US08350029B2

Reaction notes

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