Ethyl 2-acetylhexanoate → Uracil, 5-butyl-6-methyl-2-thio-

HRID 457374

반응식

HRID 457374 반응식
[Na].[NH2:2][C:3]([NH2:5])=[S:4].CC[O-].[Na+].[CH2:10]([CH:14]([C:20]([CH3:22])=O)[C:15](OCC)=[O:16])[CH2:11][CH2:12][CH3:13]>CCO>[CH2:10]([C:14]1[C:15](=[O:16])[NH:2][C:3](=[S:4])[NH:5][C:20]=1[CH3:22])[CH2:11][CH2:12][CH3:13]

참가 물질

6

반응물 4

HCID 95466Ethyl 2-acetylhexanoateHCID 2723790ThioureaHCID 2723922Sodium ethoxideHCID 5360545Sodium

생성물 1

HCID 2725680Uracil, 5-butyl-6-methyl-2-thio-

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Sodium metal (1.85 g, 80.5 mmol) is dissolved in EtOH (50 mL). Next, thiourea (5.11 g, 67.1 mmol) is added to the NaOEt solution, followed by ethyl 2-n-butylacetoacetate (2.5 g, 13.4 mmol). The reaction mixture is stirred at reflux for 3 hours and then allowed to cool to room temperature overnight. The EtOH is removed in vacuo. The residue is then suspended in H2O (50 mL) and the resulting mixture carefully treated with concentrated HCl (˜7.5 mL) just until pH 4 is reached. After stirring for 15 minutes, the suspension is filtered, and the solid thoroughly washed with H2O. Drying affords pure 5-butyl-6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one as a slightly off-white solid. 1H NMR (DMSO-d6, 300 MHz) δ 12.28 (br s, 1H), 12.05 (br s, 1H), 2.21 (m, 2H), 2.18 (s, 3H), 1.30–1.21 (m, 4H), 0.85 (t, J=6.9 Hz, 3H) ppm. MS: m/z 199 [M+1].

후처리

  1. temperatureat reflux for 3 hours
  2. customThe EtOH is removed in vacuo
  3. additionthe resulting mixture carefully treated with concentrated HCl (˜7.5 mL) just until pH 4
  4. stirringAfter stirring for 15 minutes
  5. filtrationthe suspension is filtered
  6. washthe solid thoroughly washed with H2O
  7. customDrying

출처 및 근거

ORD 기록
ord-e885f8249a94470f85893922d3660dba
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186734B2

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