Triethylamine → 2-[2-Hydroxy-3-(4-methoxy-phenyl)-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 33969Notes

Reaction equation

HRID 33969 reaction equation
[NH2:1][CH2:2][CH:3]([OH:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.C(N(CC)CC)C.Cl[C:22]1[N:27]([CH3:28])[C:26](=[O:29])[C:25]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)=[C:24]([C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)[N:23]=1>ClCCl>[OH:13][CH:3]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH2:2][NH:1][C:22]1[N:27]([CH3:28])[C:26](=[O:29])[C:25]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)=[C:24]([C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)[N:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 221851932-Chloro-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-oneHCID 597965051-Amino-3-(4-methoxyphenyl)propan-2-ol

Product 1

HCID 597965072-[2-Hydroxy-3-(4-methoxy-phenyl)-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1-amino-3-(4-methoxy-phenyl)-propan-2-ol (1.1 g, 6.1 mmol) and triethylamine in 25 mL dichloromethane was added 2-chloro-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one. The solution was stirred at room temperature for 72 h. The organic layer was washed twice with 5% sodium bicarbonate, once with brine, then dried over magnesium sulfate. The product was purified on 90 g of silica eluting with 1 to 5% methanol/dichloromethane to give a yellow foam. M+1=493.2.

Workup

  1. washThe organic layer was washed twice with 5% sodium bicarbonate, once with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe product was purified on 90 g of silica eluting with 1 to 5% methanol/dichloromethane
  4. customto give a yellow foam

Sources & evidence

ORD record
ord-5dbaebb7415046d2b6aca0c184dc0a4a
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Reaction notes

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