Sodium triacetoxyborohydride → HCID 9805331, compound

HRID 1823670Notes

Reaction equation

HRID 1823670 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]=[CH:14][CH:13]=[N: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]([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]=[CH:14][CH:13]=[N: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]=[CH:14][CH:13]=[N: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 71191659HCID 71191659, compound

Product 2

HCID 9805331HCID 9805331, compoundHCID 131725729HCID 131725729, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of 2-(1-amino-2-methyl-propyl)-3-benzyl-3-H-pyrido[2,3-d]pyrimidin-4-one (983 mg, 3.188 mmol), Na(OAc)3BH (1.352 g, 6.376 mmol) and dichloromethane (25 mL) was added a solution of t-butyl-N-(3-oxopropyl)-carbamate (714 mg, 3.51 mmol) in dichloromethane (25 mL) dropwise. The reaction mixture was stirred at room temperature for 30 minutes, diluted with 100 mL of dichlorometane, washed with saturated sodium bicarbonate, H2O, brine and dried (Na2SO4). After concentration, the desired product of Formula 108, N-{3-[1-(3-benzyl-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-2-methyl-proplyamino]-propyl}-carbamic acid tert butyl ester, was obtained as a white solid (1.45 g, 98%).

Workup

  1. washwashed with saturated sodium bicarbonate, H2O, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationAfter concentration

Sources & evidence

ORD record
ord-fa90a0971107419f8507c3d46d38fd3e
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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