Methylamine → Ethyl 6-benzyloxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate

HRID 458682노트

반응식

HRID 458682 반응식
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH2:16][C:17]([O:19]C)=O)[C:12](S(C)(=O)=O)=[N:11][C:10]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][NH2:31]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][C:17](=[O:19])[N:31]([CH3:30])[C:12]2=[N:11][C:10]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 6329MethylamineHCID 184425315-Benzyloxy-2-methanesulfonyl-1-methoxycarbonylmethyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

생성물 1

HCID 18442533Ethyl 6-benzyloxy-1-methyl-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
22 °C

실험 절차

A solution of intermediate 3, ethyl 5-(benzyloxy)-1-(methoxycarbonylmethyl)-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate, (0.790 g, 1.86 mmol) in tetrahydrofuran (10 ml) was treated with a 2 M solution of methylamine in tetrahydrofuiran (10 ml, 20.0 mmol) and the resulting mixture was stirred at 22° C. for 1 h. The solvent was then evaporated in vacuo and the residue was diluted with ethyl acetate, washed successively with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent followed by recrystallization of the solid residue from ethyl acetate/hexane gave 0.705 g (83% yield) of the title ester as white crystals; mp 167° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.34 (3H, t, J=7.1 Hz, CH3), 3.29 (3H, s, NCH3), 4.37 (2H, q, J=7.2 Hz, OCH2), 4.55 (2H, s, CH2), 5.23 (2H, s, OCH2), 7.3–7.5 (5H, m, aromatics). Anal. Calcd for C17H17N3O5: C, 59.47; H, 4.99; N, 12.23. Found: C, 59.5, H, 5.07; N, 12.40.

후처리

  1. customThe solvent was then evaporated in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed successively with saturated sodium bicarbonate, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent
  6. customfollowed by recrystallization of the solid residue from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-860ce72237134d77bd2d3a74edd10f4c
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192948B2

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