Ethyl Acetate → 2-(5-Amino-5,6,7,8-tetrahydroquinazolin-2-yl)ethanol

HRID 32128Notes

Reaction equation

HRID 32128 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[C:6]([CH2:12][CH2:13][O:14][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[N:5]=[CH:4][C:3]1=2.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O.CCOC(C)=O.CO>C1COCC1.CO>[NH2:1][CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[C:6]([CH2:12][CH2:13][OH:14])[N:5]=[CH:4][C:3]1=2

Participants

7

Reactant 4

HCID 8857Ethyl Acetate2×HCID 2724141Tetrabutylammonium FluorideHCID 21584119Ethylacetate methanolHCID 588413762-(2-(Tert-butyldiphenylsilyloxy)ethyl)-5,6,7,8-tetrahydro-quinazolin-5-amine

Product 1

HCID 588413542-(5-Amino-5,6,7,8-tetrahydroquinazolin-2-yl)ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-amino-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5,6,7,8-tetrahydro-quinazoline (570 mg, 1.32 mmol) in 10 mL of THF at 0° C. was treated with a 1 M TBAF solution in THF (1.56 mL, 1.56 mmol). After stirring at RT overnight, the reaction mixture was directly submitted to flash chromatograph (SiO2, EtOAc to EtOAc/MeOH=100:15 to EtOAc/2 M NH3 in MeOH=1:1) to give crude compound as a white solid.

Workup

  1. customto give crude compound as a white solid

Sources & evidence

ORD record
ord-ae146f918fb841879119c8360404f3ba
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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