Acetic Anhydride → HCID 136109365, 화합물

HRID 2165713노트

반응식

HRID 2165713 반응식
[CH2:1]([O:3][CH:4]([O:16][CH2:17][CH3:18])[CH2:5][CH2:6][C:7]1[C:12](=[O:13])[NH:11][C:10]([NH2:14])=[N:9][C:8]=1[NH2:15])[CH3:2].C(O[C:23](=[O:25])[CH3:24])(=O)C>N1C=CC=CC=1>[CH2:1]([O:3][CH:4]([O:16][CH2:17][CH3:18])[CH2:5][CH2:6][C:7]1[C:12](=[O:13])[NH:11][C:10]([NH:14][C:1](=[O:3])[CH3:2])=[N:9][C:8]=1[N:15]([C:23](=[O:25])[CH3:24])[C:12](=[O:13])[CH3:7])[CH3:2]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 135816675HCID 135816675, 화합물

생성물 1

HCID 136109365HCID 136109365, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A stirred mixture of 7.20 g (28.1 mmol) of 3-(2,4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propionaldehyde diethyl acetal, 30 ml of dry pyridine and 30 ml of freshly distilled acetic anhydride was heated on an oil bath at 90° for 6 hours and then stirred at ambient temperature overnight. Solution occurred within 15 minutes as a mixture of diacetyl and triacetyl pyrimidinone formed; extended reaction was required to obtain only the title compound. The solution was spin evaporated in vacuo to give an oil. Ethyl acetate was added and spin evaporated several times until a solid was obtained. The solid was dispersed in cyclohexane and collected; yield, 8.88 g (82%), mp 126°-137° (one spot on TLC). Recrystallization of a portion from cyclohexane-ethylacetate gave the analytical sample, mp 138°-139°; TLC (C6H6 :EtOH/5:1); NMR (DMSO-d6) δ1.08 (t, 6H, 2CH2CH3), 1.63 (m, 2H, CH2CH2CH), 2.13 (s, 3H, Ac), 2.27 (s, 6H, 2Ac), 2.2 (2H, CH2CH2CH, superimposed on the acetyl singlets), 3.2-3.7 (m, 4H, 2×OCH2), 4.42 (t, 1H, CH), 11.87 (br s, 2H, AcNH and HNC(O)).

후처리

  1. temperaturewas heated on an oil bath at 90° for 6 hours
  2. customformed
  3. customextended reaction

출처 및 근거

ORD 기록
ord-2f612efacab8402f8595d7c1709212df
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04940713

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