Sodium triacetoxyborohydride → {3-[1-(3-Benzyl-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propylamino]-propyl}-carbamic acid tert-butyl ester

HRID 1823692Notes

Reaction equation

HRID 1823692 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](=[N:9][CH:10]=[CH:11][N:12]=2)[N:7]=1)[CH:3]([CH3:5])[CH3:4].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[C:38]([O:42][C:43](=[O:49])[NH:44][CH2:45][CH2:46][CH:47]=O)([CH3:41])([CH3:40])[CH3:39]>ClCCl>[C:38]([O:42][C:43](=[O:49])[NH:44][CH2:45][CH2:46][CH2:47][NH: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](=[N:9][CH:10]=[CH:11][N:12]=2)[N:7]=1)[CH:3]([CH3:5])[CH3:4])([CH3:41])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10910051tert-Butyl N-(3-oxopropyl)carbamateHCID 221726212-(1-amino-2-methyl-propyl)-3-benzyl-3H-pteridin-4-one

Product 1

HCID 69315652{3-[1-(3-Benzyl-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propylamino]-propyl}-carbamic acid tert-butyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Formula 108 where R2 and R3 are H; R5 is Benzyl; R6 is Isopropyl; R6′ is H; R7is 3-Boc-amino-propyl-; X and Y are —C═; and W and Z are —N═: To a solution of dichloromethane (100 mL), 2-(1-amino-2-methyl-propyl)-3-benzyl-3H-pteridin-4-one (780 mg, 2.52 mmol) and Na(OAc)3BH (1.07 g, 5.04 mmol) was added t-butyl-N-(3-oxopropyl)-carbamate (611 mg, 3.53 mmol) at room temperature. The reaction mixture was stirred at room temperature for 3 hours, diluted with 100 mL of dichloromethane, washed with saturated sodium bicarbonate, water and brine, and dried over sodium sulfate. Concentration of the organic phase yielded the desired Boc amino product of Formula 108, {3-[1-(3-benzyl-4-oxo-3,4-dihydro-pteridin-2-yl)-2-methyl-propylamino]-propyl}-carbamic acid tert-butyl ester (1.15 g, 98%). MS (Cl) M/E: 467.3.

Workup

  1. washwashed with saturated sodium bicarbonate, water and brine
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-c84d61234610402588db85f16d18d798
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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