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 2223147노트

반응식

HRID 2223147 반응식
[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]

참가 물질

5

반응물 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

생성물 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-one수율 59.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6472c18709eb4259bfc5c373ebcadb14
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375102B2

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