Morpholine → HCID 178486773, compound

HRID 871613Notes

Reaction equation

HRID 871613 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[CH2:8][CH2:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([OH:21])=[N:16][CH:17]=[N:18]2)=[CH:13][C:12]=1[O:22][CH3:23]>C(Cl)Cl>[OH:21][C:15]1[C:14]2[C:19](=[CH:20][C:11]([O:10][CH2:9][CH2:8][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[C:12]([O:22][CH3:23])[CH:13]=2)[N:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 178486770HCID 178486770, compound

Product 1

HCID 178486773HCID 178486773, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To morpholine (5 mL) was added 7-(2-chloro-ethoxy)-6-methoxy-quinazolin-4-ol (600 mg, 2.36 mmol) from Example 35A and the mixture heated at 100° C. for 4 hours. After cooling to room temperature, the mixture was diluted with DCM and filtered. The resulting solid was washed with MeOH and H2O to give 4-hydroxy-6-methoxy-7-(2-morpholinoethoxy)quinazoline (328 mg, 1.07 mmol, 46%). 1H NMR (300 MHz, DMSO-d6) δ 12.08 (br s, 1H), 7.98 (s, 1H), 7.44 (s, 1H), 7.17 (s, 1H), 4.23 (t, 2H), 3.87 (s, 3H), 3.58 (t, 4H), 3.41-3.32 (m, 4H), 2.75 (t, 2H); LC-MS (ESI) m/z 306 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered
  3. washThe resulting solid was washed with MeOH and H2O

Sources & evidence

ORD record
ord-30b27fbc5afe421c96b7007386f9dfd4
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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