Sodium triacetoxyborohydride → HCID 69314010, compound

HRID 1823686Notes

Reaction equation

HRID 1823686 reaction equation
[NH2:1][CH:2]([C:6]1[N:7]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8](=[O:16])[C:9]2[CH:15]=[N:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[CH:3]([CH3:5])[CH3:4].[BH-](O[C:34]([CH3:36])=[O:35])(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>[NH2:44][CH2:45][CH2:46][CH2:47][N:1]([C@@H:2]([C:6]1[N:7]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8](=[O:16])[C:9]2[CH:15]=[N:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[CH:3]([CH3:5])[CH3:4])[C:34](=[O:35])[C:36]1[CH:22]=[CH:23][C:18]([CH3:17])=[CH:19][CH:20]=1.[C:38]([O:42][C:43](=[O:49])[NH:44][CH2:45][CH2:46][CH2:47][NH:1][CH:2]([C:6]1[N:7]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8](=[O:16])[C:9]2[CH:15]=[N:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[CH:3]([CH3:5])[CH3:4])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10910051tert-Butyl N-(3-oxopropyl)carbamateHCID 22172631HCID 22172631, compound

Product 2

HCID 69314010HCID 69314010, compoundYield 285.3%HCID 69316230HCID 69316230, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dichloromethane (100 mL), 2-(1-amino-2-methyl-propyl)-3-benzyl-3H-pyrido[4,3-d]pyrimidin-4-one (1.92 mmol) and Na(OAc)3BH (0.814 g, 3.84 mmol), was added t-butyl-N-(3-oxopropyl)-carbamate (0.400 g, 2.30 mmol) at room temperature. The mixture was stirred at room temperature for 3 hours, after which it was diluted with dichloromethane (100 mL), washed with saturated sodium bicarbonate, water and brine, and dried over sodium sulfate. After concentration under reduced pressure, the desired product {3-[1-(3-benzyl-4-oxo-3,4-dihydro-pyrido[4,3-d]pyrimidin-2-yl)-2-methyl-propylamino]-propyl}-carbamic acid tert-butyl ester (0.850 g, 95%) was obtained in sufficiently pure form to be carried forward for use in the next step. MS (Cl) M/E: 466.2.

Workup

  1. washwashed with saturated sodium bicarbonate, water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationAfter concentration under reduced pressure

Sources & evidence

ORD record
ord-b8741f60d699475caba100bdab24a825
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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