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

HRID 12720ノート

反応式

HRID 12720 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-ddd01cb341e9463f97cacdc3053be46d
出典データセット
uspto-grants-2010_06
特許番号
US07727988B2

反応ノート

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