Potassium Carbonate → (R)-8-Acetyl-2-{1-[(2,5-dimethyl-2H-pyrazol-3-ylmethyl)-amino]-ethyl}-3-(4-ethoxy-phenyl)-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one

HRID 2223147Notes

Reaction equation

HRID 2223147 reaction equation
[C:1]([N:4]1[C:9]2[N:10]=[C:11]([C@H:24]([NH2:26])[CH3:25])[N:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=3)[C:13](=[O:14])[C:8]=2[CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[CH2:28][C:29]1[N:33]([CH3:34])[N:32]=[C:31]([CH3:35])[CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([N:4]1[C:9]2[N:10]=[C:11]([C@H:24]([NH:26][CH2:28][C:29]3[N:33]([CH3:34])[N:32]=[C:31]([CH3:35])[CH:30]=3)[CH3:25])[N:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=3)[C:13](=[O:14])[C:8]=2[CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 534165735-(Bromomethyl)-1,3-dimethyl-1H-pyrazoleHCID 58617407(R)-8-Acetyl-2-(1-amino-ethyl)-3-(4-ethoxy-phenyl)-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one

Product 1

HCID 58617388(R)-8-Acetyl-2-{1-[(2,5-dimethyl-2H-pyrazol-3-ylmethyl)-amino]-ethyl}-3-(4-ethoxy-phenyl)-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-oneYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

D4 (70 mg, 0.20 mmol), C3 (37 mg, 0.20 mmol), and potassium carbonate (30 mg, 0.22 mmol) were stirred in dimethylformamide at room temperature overnight. The reaction mixture was partitioned between 4:1 ether:dichloromethane and water. The organic layer was washed with water and brine. It was dried over magnesium sulfate, filtered, then concentrated in vacuo. Purified by chromatography (2% to 5% methanol with 0.1% ammonium hydroxide in dichloromethane), yielding 55 mg of D5.

Workup

  1. customThe reaction mixture was partitioned between 4:1 ether
  2. washThe organic layer was washed with water and brine
  3. dry with materialIt was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurified by chromatography (2% to 5% methanol with 0.1% ammonium hydroxide in dichloromethane)

Sources & evidence

ORD record
ord-6472c18709eb4259bfc5c373ebcadb14
Source dataset
uspto-grants-2008_05
Patent number
US07375102B2

Reaction notes

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