Sodium borohydride → HCID 68079067, compound

HRID 578657Notes

Reaction equation

HRID 578657 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:30]=[O:31])[CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][N:10]=[C:9]2[NH:14][CH2:15][C:16]1[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:20][CH:21]=1)=[O:3].[Na].[BH4-].[Na+]>O1CCCC1>[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH2:30][OH:31])[CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][N:10]=[C:9]2[NH:14][CH2:15][C:16]1[CH:17]=[C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27])[CH:19]=[CH:20][CH:21]=1)=[O:3]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5360545SodiumHCID 86662384Tert-butyl [3-({[8-(aminocarbonyl)-6-formylquinazolin-4-yl]amino}methyl)phenyl]carbamate

Product 1

HCID 68079067HCID 68079067, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. customAfter workup, the product was purified by HPLC

Sources & evidence

ORD record
ord-8853057d212e439faee23fcc622921b7
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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