二甲胺 → 6-dimethylamino-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

HRID 1453

反应方程式

HRID 1453 反应方程式
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([CH2:14][C:15]#[CH:16])[C:4](=[O:17])[C:3]=1[CH3:18].[CH3:19][NH:20][CH3:21]>O1CCCC1.CCOCC>[CH3:19][N:20]([CH3:21])[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([CH2:14][C:15]#[CH:16])[C:4](=[O:17])[C:3]=1[CH3:18]

参与物

5

反应物 2

HCID 674二甲胺HCID 196907006-chloro-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

产物 1

HCID 196906956-dimethylamino-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

试剂、催化剂与溶剂 2

HCID 3283乙醚溶剂HCID 8028四氢呋喃溶剂

实验过程

To an ice cooled solution of 1.5 g (3.8 mmol) 6-chloro-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone in 4 mL of tetrahydrofuran, was added 22 mL (99 mmol) of 4.5M dimethylamine in ether portionwise (2-4 mL) over a period of 7 days. The reaction mixture was allowed to warm and stir at room temperature after each addition. The progress of the reaction was followed by gas chromatography and proceeded to 80% completion. The solvent was removed in vacuo and the residue was taken up in ether and washed twice with water. The organic layer was dried over MgSO4 and concentrated to yield 1.15 g crude solid product. Flash column chromatography on silica gel (gradient elution 25-30% ethyl acetate-hexane) afforded pure 6-dimethylamino-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (compound 23), as a white solid. 1H-NMR (CDCl3) δ 2.2(3H,s); 2.35(1H,t); 3.5(6H,s); 4.6(2H,d); 7.65(3H,m); 7.75(2H,m).

后处理

  1. temperatureto warm
  2. additionafter each addition
  3. customThe solvent was removed in vacuo
  4. washwashed twice with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customto yield 1.15 g crude solid product

来源与证据

ORD记录
ord-c771bb9653f84a339085fb2d456f388e
来源数据集
uspto-grants-1998_03
专利号
US05726124

关联笔记

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