1,3-Propanediol → HCID 178520853, compound

HRID 639968Notes

Reaction equation

HRID 639968 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][OH:6].F[C:9]1[CH:18]=[C:17]2[C:12]([C:13]([OH:19])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1>CN(C)C=O>[OH:6][CH2:5][CH2:4][CH2:3][O:7][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([OH:19])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 178518022HCID 178518022, compound

Product 1

HCID 178520853HCID 178520853, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (14.6 g, 365 mmol) was added at 0° C. to a solution of 1,3-propanediol (27.8 g, 365 mmol) in dimethylformamide (70 ml). 7-Fluoroquinazolin-4-ol (10 g, 60.9 mmol) was added portion wise and the reaction mixture heated at 60° C., then at 110° C. for 3 hours. The reaction was cooled to 0° C., quenched with water (280 ml) and adjusted to pH 5.9. The resulting suspension was filtered, washed with water then diethyl ether and dried over phosphorus pentoxide to yield 7-(3-hydroxypropoxy)quinazolin-4-ol as a white powder (12.41 g, 92% yield):

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with water (280 ml)
  3. filtrationThe resulting suspension was filtered
  4. washwashed with water
  5. dry with materialdiethyl ether and dried over phosphorus pentoxide

Sources & evidence

ORD record
ord-9ae571865cce448fba0f9fb09045576e
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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