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

HRID 1444730Notes

Reaction equation

HRID 1444730 reaction equation
[Si]([O:18][CH2:19][CH2:20][C:21]1[N:30]=[CH:29][C:28]2[CH:27]([NH2:31])[CH2:26][CH2:25][CH2:24][C:23]=2[N:22]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O.CCOC(C)=O.CO>C1COCC1.CO>[NH2:31][CH:27]1[CH2:26][CH2:25][CH2:24][C:23]2[N:22]=[C:21]([CH2:20][CH2:19][OH:18])[N:30]=[CH:29][C:28]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 2-(2-(tert-butyldiphenylsilyloxy)ethyl)-5,6,7,8-tetrahydroquinazolin-5-amine (570 mg, 1.32 mmol) in 10 mL of THF at 0° C. was treated with a 1M TBAF solution in THF (1.56 mL, 1.56 mmol). After stirring at room temperature overnight, the reaction mixture was directly submitted to flash chomatograph (SiO2, EtOAc to EtOAc/MeOH=100:15 to EtOAc/2M NH3 in MeOH=1:1) to give crude product as a white solid.

Workup

  1. customto give crude product as a white solid

Sources & evidence

ORD record
ord-5d52533add82439997f582ee0c12428b
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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