Lithium borohydride → HCID 21701554, compound

HRID 1596287Notes

Reaction equation

HRID 1596287 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:22][C:23](OCC)=[O:24])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[C:6]([F:30])[CH:5]=1>C1COCC1>[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:22][CH2:23][OH:24])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[C:6]([F:30])[CH:5]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 21701552HCID 21701552, compound

Product 1

HCID 21701554HCID 21701554, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium borohydride (150 μl of a 2M solution in THF, 0.15 mmol) was added to a solution of 4-(4-chloro-2-fluoroanilino)-7-(ethoxycarbonylmethoxy)-6-methoxyquinazoline (150 mg, 0.3 mmol) in THF (1 ml) and the mixture stirred for 1.5 hours. The reaction mixture was quenched with aqueous amonium chloride solution and extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4) and concentrated by evaporation. Hexane was added, the mixture was cooled and the precipitated solid was collected by filtration to give 4-(4-chloro-2-fluoroanilino)-7-(2-hydroxyethoxy)-6-methoxyquinazoline (30 mg, 23%).

Workup

  1. customThe reaction mixture was quenched with aqueous amonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated by evaporation
  6. additionHexane was added
  7. temperaturethe mixture was cooled
  8. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-9b8872468f034292846bab3d53e3660a
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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