Water → 5-(Benzyloxy)pyrimidin-2-amine

HRID 1442508ノート

反応式

HRID 1442508 の反応式
[CH2:1]([O:8][C:9](=[CH:12]N(C)C)[CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:17][C:18]([NH2:20])=[NH:19].[H-].[Na+].O>CN1CCCC1=O>[CH2:1]([O:8][C:9]1[CH:10]=[N:19][C:18]([NH2:20])=[N:17][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 24758Sodium hydride2 回HCID 545210022-Benzyloxy-3-(dimethylamino)acrolein

生成物 1

HCID 207483975-(Benzyloxy)pyrimidin-2-amine収率 65.5%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

2-(Benzyloxy)-3-(dimethylamino)acrylaldehyde (10.9 g, 53 mmol) was dissolved in N-methylpyrrolidone (85 mL), the solution was added with guanidine hydrochloride (15.3 g, 160 mmol), and then the mixture was added with sodium hydride (50% in oil, 15.3 g, 320 mmol) with stirring on an ice bath, and stirred on an oil bath at 80° C. for 1 hour. The reaction mixture was added with water on an ice bath to decompose excessive sodium hydride, and then extracted with ether and water, and the organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:acetone=10:1→4:1→2:1→1:1), and the eluate was concentrated under reduced pressure. Then, the resulting residue was washed with ether-hexane, and taken by filtration to obtain 5-(benzyloxy)pyrimidin-2-amine (6.99 g, 65%) as a pale yellow solid.

後処理

  1. stirringstirred on an oil bath at 80° C. for 1 hour
  2. extractionextracted with ether and water
  3. washthe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:acetone=10:1→4:1→2:1→1:1)
  7. concentrationthe eluate was concentrated under reduced pressure
  8. washThen, the resulting residue was washed with ether-hexane
  9. filtrationtaken by filtration

出典と根拠

ORDレコード
ord-31d09ee939924d61aefc61845237fb38
出典データセット
uspto-grants-2010_02
特許番号
US07659271B2

反応ノート

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