Sodium hydride → HCID 135493222, compound

HRID 890982Notes

Reaction equation

HRID 890982 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[H-].[Na+].F[C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:23])[NH:18][CH:19]=[N:20]2)=[CH:15][CH:14]=1>CN(C=O)C>[O:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][O:1][C:13]2[CH:22]=[C:21]3[C:16]([C:17](=[O:23])[NH:18][CH:19]=[N:20]3)=[CH:15][CH:14]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 611632-MorpholinoethanolHCID 1353984967-Fluoroquinazolin-4(3H)-one

Product 1

HCID 135493222HCID 135493222, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of N-(2-hydroxyethyl)morpholine (2.66 ml), sodium hydride (60% dispersion in mineral oil, 0.88 g) and DMF (25 ml) was warmed to 50° C. for 3 minutes. The resulting solution was allowed to cool for 10 minutes before a solution of 7-fluoro-3,4-dihydroquinazolin-4-one (1.64 g) in DMF (25 ml) was added and the resultant mixture was heated to 125° C. for 18 hours. The solvent was evaporated and the residue was partitioned between methylene chloride and 2N hydrochloric acid solution. The organic phase was dried and evaporated to give 7-(2-morpholinoethoxy)-3,4-dihydroquinazolin-4-one (1.58 g); NMR Spectrum: (CDCl3) 2.6 (t, 4H), 2.87 (t, 2H), 3.73 (t, 4H), 4.25 (t, 2H), 7.12 (m, 2H), 8.07 (s, 1H), 8.19 (d, 1H); Mass Spectrum: M+H+ 276.

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between methylene chloride and 2N hydrochloric acid solution
  4. customThe organic phase was dried
  5. customevaporated

Sources & evidence

ORD record
ord-c3598e66f9de44309cac1759ab13caaa
Source dataset
uspto-grants-2006_02
Patent number
US07001904B1

Reaction notes

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