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

HRID 1461

反応式

HRID 1461 の反応式
[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]

参加物

4

反応物 2

HCID 14923Ammonium HydroxideHCID 196906976-ethyl-5-methoxycarbonylmethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-f44bdc8cc42c4333808efcfd30ed387a
出典データセット
uspto-grants-1998_03
特許番号
US05726124

関連ノート

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