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

HRID 1463

반응식

HRID 1463 반응식
[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]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 196906705-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone2회

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b5423c5215ee415abe3ef0b650a1ea4e
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726124

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