Potassium Carbonate → 5-(6-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione

HRID 12716ノート

反応式

HRID 12716 の反応式
Cl.[Cl:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH: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[N:8]=[CH:7][C:6]([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:5][CH:4]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 866159485-(6-Chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride

生成物 1

HCID 589941995-(6-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

A mixture of 5-(6-chloro-pyridin-3-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep91, 1.05 g, 4.10 mmol), and K2CO3 (565 mg, 4.10 mmol) in DMF (20 ml) was stirred 20 minutes at room temperature. 3-Bromo-1,1dimethoxy-propane (635 μl, 4.65 mmol) was added in three portions over 6 days. Solvent was then removed under vacuum at 40° C. and the residue washed once with petroleum ether and twice 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 534 mg of the title compound as a white solid (40% yield).

後処理

  1. customSolvent was then removed under vacuum at 40° C.
  2. washthe residue washed once with petroleum ether and twice with ethyl acetate
  3. dry with materialEthyl acetate phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was purified by flash chromatography
  7. washeluting with DCM-MeOH—NH4OH (98:2:0.2)

出典と根拠

ORDレコード
ord-cbb08e8ad456443e8d4d55ae46eccee5
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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