HCID 86647829, compound → HCID 86647828, compound

HRID 241072Notes

Reaction equation

HRID 241072 reaction equation
[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]([CH:12]=[O:13])[CH2:7][C:6]=2[N:5]=[CH:4][N:3]=1.[CH3:14][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]([CH:12]([OH:13])[CH3:14])[CH2:7][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 86647829HCID 86647829, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 86647828HCID 86647828, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 4-chloro-5,6,7,8-tetrahydroquinazoline-7-carbaldehyde (0.10 g, 0.51 mmol) in THF (5 mL) was added a solution of MeMgBr (3.0 M in ethyl ether, 0.40 mL, 1.2 mmol). The resulting mixture was stirred at ambient temperature for 30 minutes and then partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography provided 1-(4-chloro-5,6,7,8-tetrahydroquinazolin-7-yl)ethanol (0.09 g, 83% yield) as a waxy solid. MS (ES) for C10H13ClN2O: 213 (MH+).

Workup

  1. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-65b80c6c8e814176b35be0519df91643
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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