Sodium triacetoxyborohydride → (2-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester

HRID 1350621Notes

Reaction equation

HRID 1350621 reaction equation
[NH2:1][CH:2]([C:6]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](=[O:23])[C:13]2[C:8](=[CH:9][C:10]([Cl:24])=[CH:11][CH:12]=2)[N:7]=1)[CH:3]([CH3:5])[CH3:4].[C:25]([O:29][C:30](=[O:37])[NH:31][C:32]([CH3:36])([CH3:35])[CH:33]=O)([CH3:28])([CH3:27])[CH3:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:25]([O:29][C:30](=[O:37])[NH:31][C:32]([CH3:36])([CH3:35])[CH2:33][NH:1][CH:2]([C:6]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:14](=[O:23])[C:13]2[C:8](=[CH:9][C:10]([Cl:24])=[CH:11][CH:12]=2)[N:7]=1)[CH:3]([CH3:5])[CH3:4])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamateHCID 222387982-(1-amino-2-methylpropyl)-3-benzyl-7-chloroquinazolin-4(3H)-one

Product 1

HCID 69074256(2-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1-amino-2-methyl-propyl)-3-benzyl-7-chloro-3H-quinazolin-4-one (WO 0130768) (1.09 g, 3.19 mmol) and (1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (Seki et. al. Chem. Pharm. Bull. 1996, 44, 2061) (0.59 g, 3.19 mmol) in dichloromethane (80 mL) was added sodium triacetoxyborohydride (1.01 g, 4.79 mmol). The resultant cloudy mixture was maintained at ambient temperature for 4 hours, at which time it was quenched with brine (75 mL) and stirred vigorously for 10 minutes. The aqueous layer was extracted with dichloromethane (50 mL) and the combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give (±)-{2-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (1.62 g, 99%) as a yellow solid which was used in the subsequent step without purification.

Workup

  1. customwas quenched with brine (75 mL)
  2. extractionThe aqueous layer was extracted with dichloromethane (50 mL)
  3. dry with materialthe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b9e4030695da492999c1835150dfaebc
Source dataset
uspto-grants-2007_05
Patent number
US07214800B2

Reaction notes

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