Methanol → 8-Hydroxy-2-methyl-4-phenyl-quinazoline

HRID 640787Notes

Reaction equation

HRID 640787 reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH3:15])[N:11]=[C:10]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C)C.B(Cl)(Cl)Cl.CO>ClCCl>[OH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH3:15])[N:11]=[C:10]2[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 592566498-Isopropoxy-2-methyl-4-phenyl-quinazoline

Product 1

HCID 592566558-Hydroxy-2-methyl-4-phenyl-quinazoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 8-isopropoxy-2-methyl-4-phenyl-quinazoline (36) (0.34 mmol) in dichloromethane (2 mL) at −78° C. was added BCl3 (1.36 mL of a 1 M solution in dichloromethane, 1.36 mmol). The reaction mixture was allowed to warm to RT (over 2 h) and stirred for a further 2 h. MeOH (5 mL) was added and the mixture was concentrated to dryness. The process was repeated four times. Further washing of the remaining residue with diethyl ether (2 mL×3) provided 8-hydroxy-2-methyl-4-phenyl-quinazoline (A24).

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. washFurther washing of the remaining residue with diethyl ether (2 mL×3)

Sources & evidence

ORD record
ord-a4ee40e22a8243b296e10c0f891489ae
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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