tert-Butyl[1-(5-chloro-2-methoxy-4-methyl-3-vinylphenyl)ethyl]carbamate → 1-(5-Chloro-2-methoxy-4-methyl-3-vinylphenyl)ethanamine hydrochloride

HRID 511009Notes

Reaction equation

HRID 511009 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([CH3:17])=[C:12]([CH:18]=[CH2:19])[C:11]=1[O:20][CH3:21])[CH3:9])(C)(C)C>Cl>[ClH:16].[Cl:16][C:14]1[C:13]([CH3:17])=[C:12]([CH:18]=[CH2:19])[C:11]([O:20][CH3:21])=[C:10]([CH:8]([NH2:7])[CH3:9])[CH:15]=1

Participants

3

Reactant 1

HCID 123890412tert-Butyl[1-(5-chloro-2-methoxy-4-methyl-3-vinylphenyl)ethyl]carbamate

Product 1

HCID 866669231-(5-Chloro-2-methoxy-4-methyl-3-vinylphenyl)ethanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl[1-(5-chloro-2-methoxy-4-methyl-3-vinylphenyl)ethyl]carbamate was stirred in 4 N HCl (1.0 mL) for 30 min and evaporated to give 1-(5-chloro-2-methoxy-4-methyl-3-vinylphenyl)ethanamine hydrochloride (480 mg, 1.8 mmol) which was stirred in 1-butanol (86 mL), with DIPEA (1.6 mL, 9.1 mmol) and 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (650 mg, 2.7 mmol, from Example 176, Step 4). The reaction mixture was heated at 120° C. for 2 hours. The reaction mixture was cooled to room temperature and extracted with EtOAc. The extracts were washed with brine and evaporated. Purification on silica gel using 0-50% EtOAc in hexane gave the desired compound (780 mg, 100%). LCMS calculated for C22H27ClN5O2 (M+H)+: m/z=428.2. found: 428.1.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-2f25a4ae0fe2467caf7563df3c18c249
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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