Sodium hydride → HCID 58739081, 화합물

HRID 720289노트

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HRID 720289 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](S(C)(=O)=O)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2].[CH3:26][C:27]1[N:31]=[CH:30][NH:29][N:28]=1.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:29]2[CH:30]=[N:31][C:27]([CH3:26])=[N:28]2)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 21060065HCID 21060065, 화합물HCID 178433329HCID 178433329, 화합물

생성물 1

HCID 58739081HCID 58739081, 화합물수율 35.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
24 °C

실험 절차

A solution of 5-benzyloxy-2-methanesulfonyl-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (1.00 g, 2.73 mmol) and 3-methyl-1H-[1,2,4]triazole (0.272 g, 3.27 mmol) in dry N,N-dimethylformamide (10 ml) at 0° C. was treated with sodium hydride (0.16 g of a 60% dispersion in mineral oil, 4.0 mmol) and the resulting mixture was stirred at 0° C. for 30 min and at 24° C. for another 30 min. The reaction mixture was then quenched with acetic acid (0.2 ml) and the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and chromatography on silica gel (elution toluene-acetone 90:10 to 85:15) first gave 0.358 g (35% yield) of 5-benzyloxy-1-methyl-2-(3-methyl-[1,2,4]triazol-1-yl)-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.34 (3H, t, J=7.1 Hz, CH3), 2.51 (3H, s, CH3), 3.73 (3H, s, NCH3), 4.37 (2H, q, J=7.1 Hz, CH2), 5.37 (2H, s, OCH2), 7.40 (3H, m, aromatics), 7.50 (2H, m, aromatics), 8.71 (1H, s, CH). HRMS (FAB POS) calculated for C18H20N5O4 [M+H+]: 370.14. found: 370.14. The following fractions then gave 0.395 g (39% yield) of 5-benzyloxy-1-methyl-2-(5-methyl-[1,2,4]triazol-1-yl)-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.33 (3H, t, J=7.0 Hz, CH3), 2.67 (3H, s, CH3), 3.52 (3H, s, NCH3), 4.37 (2H, q, J=7.0 Hz, CH2), 5.41 (2H, s, OCH2), 7.40 (3H, m, aromatics), 7.51 (2H, m, aromatics), 8.00 (1H, s, CH). HRMS (FAB POS) calculated for C18H20N5O4 [M+H+]: 370.14. found: 370.14.

후처리

  1. customThe reaction mixture was then quenched with acetic acid (0.2 ml)
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried over anhydrous magnesium sulfate

출처 및 근거

ORD 기록
ord-ced80ad8de7f429795336b807497710f
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135467B2

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