Potassium Carbonate → 5-(2-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione

HRID 12720노트

반응식

HRID 12720 반응식
Cl.[Cl:2][C:3]1[C:8]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28]>CN(C=O)C>[Cl:2][C:3]1[C:8]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[N:13]([CH2:24][CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28])[CH:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 866159495-(2-Chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride

생성물 1

HCID 589942035-(2-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 5-(2-chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride salt (Prep95, 803 mg, 3.10 mmol) and K2CO3 (428 mg, 3.10 mmol) in DMF (15 ml), 90% 3-bromo-1,1dimethoxy-propane (516 μl, 3.41 mmol) was added in three portions over 5 days. The mixture was contemporarily stirred at room temperature. Solvent was then removed in vacuum at 40° C. The residue washed with petroleum ether and then with ethyl acetate. Ethyl acetate phase was dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography eluting with DCM-MeOH—NH4OH (98:2:0.2) to give 400 mg of the final compound as a white solid (40% yield)

후처리

  1. additionwas added in three portions over 5 days
  2. customSolvent was then removed in vacuum at 40° C
  3. washThe residue washed with petroleum ether
  4. dry with materialEthyl acetate phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was purified by flash chromatography
  8. washeluting with DCM-MeOH—NH4OH (98:2:0.2)

출처 및 근거

ORD 기록
ord-ddd01cb341e9463f97cacdc3053be46d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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