Methanol → HCID 86647826, compound

HRID 241071Notes

Reaction equation

HRID 241071 reaction equation
[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]([CH:12]=C)[CH2:7][C:6]=2[N:5]=[CH:4][N:3]=1.[BH4-].[Na+].C[OH:17]>ClCCl>[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]([CH2:12][OH:17])[CH2:7][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 866478274-Chloro-7-vinyl-5,6,7,8-tetrahydroquinazoline

Product 1

HCID 86647826HCID 86647826, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ozone was bubbled through a cooled (−78° C.) solution of 4-chloro-7-vinyl-5,6,7,8-tetrahydroquinazoline (reagent preparation 3, 0.35 g, 1.8 mmol) in methanol (5 mL) and dichloromethane (30 mL) until a blue color persisted. The solution was then sparged with N2 for 10 minutes and sodium borohydride (0.14 g, 3.6 mmol) was added portionwise. After 30 minutes the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and then concentrated in vacuo to provide (4-chloro-5,6,7,8-tetrahydroquinazolin-7-yl)methanol (0.32 g, 90% yield) as a waxy solid. MS (ES) for C9H11ClN2O: 199 (MH+).

Workup

  1. customOzone was bubbled through
  2. customThe solution was then sparged with N2 for 10 minutes
  3. customAfter 30 minutes the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ae047abe0194348bcddfb7caba16665
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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