盐酸乙脒 → 2-methyl-6-phenyl-5-propargyl-4(3H)-pyrimidinone

HRID 488336

反应方程式

HRID 488336 反应方程式
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].C[O-].[Na+].[C:9]([CH:17]([CH2:23][C:24]#[CH:25])[C:18](OCC)=[O:19])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO.C1(C)C=CC=CC=1>[CH3:3][C:2]1[NH:5][C:18](=[O:19])[C:17]([CH2:23][C:24]#[CH:25])=[C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:4]=1

参与物

6

反应物 3

HCID 67170盐酸乙脒HCID 10942334甲醇钠HCID 11009766Ethyl 2-benzoylpent-4-ynoate

产物 1

HCID 1356894052-methyl-6-phenyl-5-propargyl-4(3H)-pyrimidinone收率 29.2%

试剂、催化剂与溶剂 2

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂HCID 1140甲苯溶剂

实验过程

To a stirred suspension of 8.00 g (84.6 mmol) of acetamidine hydrochloride in 100 mL of methanol was added 4.56 g (84.4 mmol) of solid sodium methoxide. The mixture was stirred for 40 min at room temperature and rotovaped to remove the methanol. The residue was suspended in 75 mL of ethanol and a solution of 6.19 g (26.9 mmol) of ethyl 2-benzoyl-pent-4-ynoate in 75 mL of toluene was added. The mixture was heated to reflux with a Dean Stark trap and the first 80 mL of distillate was collected and discarded. An 80 mL portion of toluene was added and the mixture was heated at reflux for two weeks. The mixture was allowed to cool, diluted with 70 mL of ether and extracted with two 50 mL portions of 5% aqueous sodium hydroxide. The aqueous extracts were acidified to pH 1 and washed with two 75 mL portions of ethyl acetate. The pH of the aqueous phase was adjusted to 10 and the white precipitate that formed was collected by filtration. Drying furnished 1.76 g (29%) of 2-methyl-6-phenyl-5-propargyl-4(3H)-pyrimidinone, mp 220°-225° C., 1H-NMR (d6-DMSO) δ 2.3 (3H,s), 2.68(1H,t,J=4), 3.20(2H, d,J=4), 7.45(3H,m), 7.65(2H,m).

后处理

  1. customto remove the methanol
  2. temperatureThe mixture was heated
  3. temperatureto reflux with a Dean Stark trap
  4. distillationthe first 80 mL of distillate was collected
  5. additionAn 80 mL portion of toluene was added
  6. temperaturethe mixture was heated
  7. temperatureat reflux for two weeks
  8. temperatureto cool
  9. additiondiluted with 70 mL of ether
  10. extractionextracted with two 50 mL portions of 5% aqueous sodium hydroxide
  11. washwashed with two 75 mL portions of ethyl acetate
  12. customthe white precipitate that formed
  13. filtrationwas collected by filtration
  14. customDrying

来源与证据

ORD记录
ord-0148953e6f8942d8bc0a8fe8a5c2878a
来源数据集
uspto-grants-1994_03
专利号
US05298481

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