Acetic Acid → 3-benzyl-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-2,4,6-trimethyl-4,6-dihydropyrimido[5,4-c]-1,8-naphthyridin-5(3H)-one

HRID 13846Notes

Reaction equation

HRID 13846 reaction equation
[C:1]([C:4]1[C:5](=[O:34])[N:6]([CH3:33])[C:7]2[C:12]([C:13]=1[NH:14][C:15](=O)[CH3:16])=[CH:11][C:10]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[C:9]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32])[N:8]=2)(=O)[CH3:2].[CH2:35]([NH2:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.C(Cl)Cl>[CH2:35]([N:42]1[CH:1]([CH3:2])[C:4]2[C:5](=[O:34])[N:6]([CH3:33])[C:7]3[N:8]=[C:9]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=4[Cl:32])[C:10]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)=[CH:11][C:12]=3[C:13]=2[N:14]=[C:15]1[CH3:16])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 11386747Naphthyridinone

Product 1

HCID 588101233-benzyl-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-2,4,6-trimethyl-4,6-dihydropyrimido[5,4-c]-1,8-naphthyridin-5(3H)-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

The product of Example 1 (80 mg) in 1,2-dichlorethane (1.5 mL) was combined with benzyl amine (16 μL), sodium triacetoxyborohydride (32 mg) and acetic acid (8.5 μL). The reaction was stirred for two days at room temperature. The reaction mixture was diluted with CH2Cl2 and washed with aqueous NaOH (1 M) and brine. The concentrated residue was purified by preparative TLC on silica gel eluted with 30% EtOAc in CH2Cl2 affording the title compound. HPLC/MS: 587.1 (M+1), 589.1 (M+3); Rt=3.86 min.

Workup

  1. washwashed with aqueous NaOH (1 M) and brine
  2. customThe concentrated residue was purified by preparative TLC on silica gel
  3. washeluted with 30% EtOAc in CH2Cl2 affording the title compound

Sources & evidence

ORD record
ord-1e2d4e90a2324ca691792e7abbe38fab
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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