吡啶 → 6-ethyl-5-cyanomethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

HRID 1463

反应方程式

HRID 1463 反应方程式
[NH2:1][C:2]([CH2:4][C:5]1[C:6](=[O:22])[N:7]([CH2:19][C:20]#[CH:21])[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][C:10]=1[CH2:11][CH3:12])=O.N1C=CC=[CH:25][CH:24]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1.CCOCC>[CH2:11]([C:10]1([CH2:24][CH3:25])[N:9]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:7]([CH2:19][C:20]#[CH:21])[C:6](=[O:22])[CH:5]1[CH2:4][C:2]#[N:1])[CH3:12]

参与物

6

反应物 3

HCID 1049吡啶HCID 9845三氟乙酸酐HCID 196906705-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone2 次

产物 1

HCID 196906746-ethyl-5-cyanomethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone收率 49.8%

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

A stirred suspension of 0.25 g (0.85 mmol) of 5-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 275) in 12 mL of THF was cooled in an icebath and 0.15 mL (1.9 mmol) of pyridine was added followed by 0.13 mL (0.92 mmol) of trifluoroacetic anhydride. The mixture was stirred in the ice bath for 4 h, diluted with 80 mL of ether, washed with 20 mL of saturated aqueous NaHCO3 and dried over MgSO4. Removal of the solvent left 0.24 g of crude product as a yellow solid. Flash chromatography on 30 g of silica gel, eluting sequentially with 50, 75 and 100% ether in hexanes afforded 0.13 g of 6-ethyl-5-cyanomethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 277) as a white solid, m.p. 178°-180° C. 1 H-NMR (CDCl3) 1.3(3H,t), 2.4(1H,t), 2.75(2H,q), 3.75(2H,s), 4.6(2H,d), 7.55(3H,m), 7.7(2H,m).

后处理

  1. additionwas added
  2. washwashed with 20 mL of saturated aqueous NaHCO3
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent
  5. waitleft 0.24 g of crude product as a yellow solid
  6. washFlash chromatography on 30 g of silica gel, eluting sequentially with 50, 75 and 100% ether in hexanes

来源与证据

ORD记录
ord-b5423c5215ee415abe3ef0b650a1ea4e
来源数据集
uspto-grants-1998_03
专利号
US05726124

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