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

HRID 33974Notes

Reaction equation

HRID 33974 reaction equation
[NH2:1][CH2:2][CH:3]([OH:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.Cl[C:20]1[N:25]([CH3:26])[C:24](=[O:27])[C:23]([C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)=[C:22]([C:38]2[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=2)[N:21]=1>ClCCl.C(OCC)(=O)C>[OH:11][CH:3]([CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:2][NH:1][C:20]1[N:25]([CH3:26])[C:24](=[O:27])[C:23]([C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)=[C:22]([C:38]2[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=2)[N:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 37580461-Amino-3-phenylpropan-2-olHCID 221851932-Chloro-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Product 1

HCID 116626342-(2-Hydroxy-3-phenyl-propylamino)-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 1-amino-3-phenyl-propan-2-ol (0.51 g, 3.3 mmol) and triethylamine (0.45 mL, 3.3 mmol) in 20 mL dichloromethane was added (0.92 g, 2.6 mmol) 2-chloro-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one. The solution was stirred for 18 h at room temperature. The solution was diluted with ethyl acetate and washed with 5% sodium bicarbonate. The organic layer was dried over magnesium sulfate and purified on 10 g silica eluting product with 0 to 5% methanol/dichloromethane to give a pale yellow solid. M+1=463.2.

Workup

  1. washwashed with 5% sodium bicarbonate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. custompurified on 10 g silica eluting product with 0 to 5% methanol/dichloromethane
  4. customto give a pale yellow solid

Sources & evidence

ORD record
ord-319e5d54cc6d43b387e915df5042ce57
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Reaction notes

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