Guanidine Hydrochloride → HCID 68671207、化合物

HRID 2071047ノート

反応式

HRID 2071047 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 68671207HCID 68671207、化合物収率 39.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-948049866d2b44f7bf7716d4d6962a76
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

読み込み中…