Guanidine Hydrochloride → HCID 68671207, 화합물

HRID 2071047노트

반응식

HRID 2071047 반응식
[CH3:1][O:2][CH2:3][C:4](=O)[CH2:5][C:6](=O)[CH:7]([CH3:9])[CH3:8].Cl.[NH2:13][C:14]([NH2:16])=[NH:15].C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[CH:7]([C:6]1[CH:5]=[C:4]([CH2:3][O:2][CH3:1])[N:15]=[C:14]([NH2:16])[N:13]=1)([CH3:9])[CH3:8]

참가 물질

6

반응물 3

HCID 5742Guanidine HydrochlorideHCID 10340Sodium CarbonateHCID 100121541-Methoxy-5-methylhexane-2,4-dione

생성물 1

HCID 68671207HCID 68671207, 화합물수율 39.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a stirred solution of 1-methoxy-5-methylhexane-2,4-dione (1.08 g, 6.8 mmol) in EtOH (15 mL) was added guanidine hydrochloride (1.3 g, 13.7 mmol). 5 min later, a solution of Na2CO3 (1.45 g, 13.7 mmol) in H2O was added and the resulting mixture was heated to reflux for 20 h. The reaction was cooled to room temperature and the solvent was removed. The residue was dissolved in EtOAc (20 mL) and H2O (20 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (50% EtOAc in hexanes) to provide 4-isopropyl-6-(methoxymethyl)pyrimidin-2-amine (482 mg, 39%). 1H NMR (CDCl3): d 6.43 (s, 1H), 6.11 (s, 2H), 4.16 (s, 2H), 3.26 (s, 3H), 2.56-2.66 (m, 1H), 1.03 (d, J=6.9 Hz, 6H).

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 20 h
  3. customthe solvent was removed
  4. dissolutionThe residue was dissolved in EtOAc (20 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-948049866d2b44f7bf7716d4d6962a76
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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