Hydrochloric Acid → 5,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone

HRID 1457

반응식

HRID 1457 반응식
[CH2:1]([C:3]1[C:4](=[O:25])[N:5]([CH2:22][C:23]#[CH:24])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]3OCC[O:18]3)[CH:12]=2)=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2].Cl.CCOCC.O>C(OCC)(=O)C.CCCCCC>[CH2:1]([C:3]1[C:4](=[O:25])[N:5]([CH2:22][C:23]#[CH:24])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[CH:12]=2)=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 218084975,6-diethyl-2-[3-(2-dioxolanyl)phenyl]-3-propargyl-4(3H)-pyrimidinone

생성물 1

HCID 196906845,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone수율 86.4%

시약·촉매·용매 2

HCID 8058Hexane용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of 2.3 g (6.8 mmol) of 5,6-diethyl-2-[3-(2-dioxolanyl)phenyl]-3-propargyl-4(3H)-pyrimidinone in 1 mL of ethyl acetate was added 50 mL of 6M hydrochloric acid and the mixture was stirred for 4 hours. The reaction was followed by gas chromatography and TLC(20% ethyl acetate in hexane). Upon completion of reaction, 75 mL of ether and 150 mL of water were added to the reaction mixture. The layers were separated and the aqueous layer was extracted twice with 50 mL of ether. The organic layers were combined, dried over MgSO4 and concentrated to yield 1.73 g of 5,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone (Compound 69) as a yellow oil (86%), which solidified on standing. Mp.=82°-86° C. 1H-NMR (CDCl3) δ 1.25(6H,m), 2.4(1H,t), 2.65(4H,q), 4.6(2H,d), 7.7(1H,t), 8.05(2H,m), 8.25(1H,s), 10.15(1H,s).

후처리

  1. additionwere added to the reaction mixture
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with 50 mL of ether
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-febb9432bc444d1b8660781f308ba31e
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726124

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