Sodium borohydride → Tert-butyl [3-({[8-(aminocarbonyl)-6-(hydroxymethyl)quinazolin-4-yl]amino}methyl)phenyl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	Sodium borohydride	HCID 4311764	—
Reactant	Sodium	HCID 5360545	—
Reactant	Tert-butyl [3-({[8-(aminocarbonyl)-6-formylquinazolin-4-yl]amino}methyl)phenyl]carbamate	HCID 86662384	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Tert-butyl [3-({[8-(aminocarbonyl)-6-(hydroxymethyl)quinazolin-4-yl]amino}methyl)phenyl]carbamate	HCID 68079067	67.5%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a solution of tert-butyl [3-({[8-(aminocarbonyl)-6-formylquinazolin-4-yl]amino}methyl)phenyl]carbamate (90.00 mg; 0.21 mmol; 1.00 eq.) in tetrahydrofuran (2.00 ml) added sodium added sodium borohydride (4.04 mg; 0.11 mmol; 0.50 eq.). The reaction mixture was stirred at 0° C. for 1 h. After workup, the product was purified by HPLC to get tert-butyl [3-({[8-(aminocarbonyl)-6-(hydroxymethyl)quinazolin-4-yl]amino}methyl)phenyl]carbamate (60 mg, 66%) MS (M+1) 424.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09040560B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-8853057d212e439faee23fcc622921b7
Source note	uspto-grants-2015_05