3-Phenyl-2,2-dimethyl-1,3-propanediamine → 2-((-3-Amino-2 2-dimethyl-3-phenylpropyl)-amino)-3-methyl-5-(3-methylphenyl)-6-(4-pyridyl)-4(3H)-pyrimidinone Hydrochloride

HRID 480440Notes

Reaction equation

HRID 480440 reaction equation
[Cl:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=2)=[C:4]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[N:3]=1.[C:23]1([CH:29]([NH2:35])[C:30]([CH3:34])([CH3:33])[CH2:31][NH2:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C>[ClH:1].[NH2:35][CH:29]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:30]([CH3:34])([CH3:33])[CH2:31][NH:32][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=2)=[C:4]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[N:3]=1

Participants

4

Reactant 2

HCID 102616653-Phenyl-2,2-dimethyl-1,3-propanediamineHCID 161156882-Chloro-3-methyl-6-pyridin-4-yl-5-m-tolyl-3H-pyrimidin-4-one

Product 1

HCID 187679282-((-3-Amino-2 2-dimethyl-3-phenylpropyl)-amino)-3-methyl-5-(3-methylphenyl)-6-(4-pyridyl)-4(3H)-pyrimidinone Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-3-methyl-5-(3-methylphenyl)-6-(4-pyridyl)-4(3H)-pyrimidinone (228 mg, 0.73 mmol) and 3-phenyl-2,2-dimethyl-1,3-propanediamine (178 mg, 1 mmol) (prepared according to: W. Ten Hoeve and H. Wynberg, Synth. Commun. 24 (15), 2215-2221, 1994) in ethanol (4 ml) was stirred at room temperature for 16 h. The solvent was evaporated and the crude product purified by column chromatography on silica gel. MS (m/z): 454 (M+H)+; C28H31N5O requir. 453.6 (free base).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-da205d230cc641cd84c46f1bc5610e96
Source dataset
uspto-grants-2003_11
Patent number
US06649604B2

Reaction notes

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