Ethylacetate methanol → 2-(2-(Tert-butyldiphenylsilyloxy)ethyl)-5,6,7,8-tetrahydro-quinazolin-5-amine

HRID 1444729Notes

Reaction equation

HRID 1444729 reaction equation
[N:1]([CH:4]1[CH2:13][CH2:12][CH2:11][C:10]2[N:9]=[C:8]([CH2:14][CH2:15][O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:7]=[CH:6][C:5]1=2)=[N+]=[N-].CCOC(C)=O.CO>CCOC(C)=O.CO.[Pd]>[Si:17]([O:16][CH2:15][CH2:14][C:8]1[N:7]=[CH:6][C:5]2[CH:4]([NH2:1])[CH2:13][CH2:12][CH2:11][C:10]=2[N:9]=1)([C:30]([CH3:33])([CH3:31])[CH3:32])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 21584119Ethylacetate methanolHCID 579324975-Azido-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-5,6,7,8-tetrahydroquinazoline

Product 1

HCID 588413762-(2-(Tert-butyldiphenylsilyloxy)ethyl)-5,6,7,8-tetrahydro-quinazolin-5-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

A suspension of 80 mg of Pd/C (10% w/w) in a solution of 5-azido-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-5,6,7,8-tetrahydroquinazoline (800 mg, 1.75 mmol) in 30 mL of EtOAc was stirred under H2 atmosphere overnight. The reaction mixture was then directly submitted to flash chomatograph (SiO2, EtOAc to EtOAc/MeOH=100:15 to EtOAc/2M NH3 in MeOH=2:1) to give the desired product as a white solid.

Sources & evidence

ORD record
ord-ad155d8156d645c2b1435642e341acbf
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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