Ammonium Hydroxide → 5-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

HRID 1461

반응식

HRID 1461 반응식
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]([CH2:15][C:16]#[CH:17])[C:5](=[O:18])[C:4]=1[CH2:19][C:20]([O:22]C)=O)[CH3:2].[NH4+:24].[OH-]>C1COCC1>[NH2:24][C:20]([CH2:19][C:4]1[C:5](=[O:18])[N:6]([CH2:15][C:16]#[CH:17])[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:8][C:3]=1[CH2:1][CH3:2])=[O:22]

참가 물질

4

반응물 2

HCID 14923Ammonium HydroxideHCID 196906976-ethyl-5-methoxycarbonylmethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone2회

생성물 1

HCID 196906705-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 1.75 g (5.7 mmol) of 6-ethyl-5-methoxycarbonylmethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 105) in 100 mL of THF was added 200 mL of concentrated aqueous NH4OH. The mixture was stirred for 2 weeks and the bulk of the THF was removed on the rotovap. The mixture was shaken with 100 mL of ethyl acetate and filtered. The solid collected was dried in a vacuum oven at 50° C. to afford 0.57 g of 5-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 275), m.p. 196°-198° C. 1H-NMR (d6 -DMSO) 1.15(3H,t), 2.5(2H,q), 3.2(1H,t), 3.4(2H,s), 4.55(2H,d), 6.9(1H,br s), 7.35(1H,br s), 7.55(3H,m), 7.7(2H,m). The aqueous layer of the filtrate was extracted with two additional 100 mL portions of ethyl acetate. The combined ethyl acetate extracts were dried over MgSO4 and rotovaped to afford a further 0.54 g of Compound 275.

후처리

  1. customthe bulk of the THF was removed on the rotovap
  2. stirringThe mixture was shaken with 100 mL of ethyl acetate
  3. filtrationfiltered
  4. customThe solid collected
  5. customwas dried in a vacuum oven at 50° C.

출처 및 근거

ORD 기록
ord-f44bdc8cc42c4333808efcfd30ed387a
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726124

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