Hydrochloric Acid → 4-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

HRID 270704

反応式

HRID 270704 の反応式
[NH2:1][C:2]1[C:7]([C:8]#N)=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl.C([O-])([O-])=[O:24].[Na+].[Na+]>C1COCC1>[NH2:1][C:2]1[C:7]([CH:8]=[O:24])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2957574-Amino-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehyde収率 53.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-amino-2-(methylthio)pyrimidine-5-carbonitrile (3.0 g, 18.05 mmol) in THF (100 mL) is added diisobutylaluminum hydride (41.52 mL, 1.0 M in CH2Cl2, 41.52 mmol) at 0° C. After the mixture is stirred for 2.5 hours at 0° C., hydrochloric acid (2N, 30 mL) is added and stirring is continued for 20 minutes. To the reaction mixture is added saturated Na2CO3 until a pH of 8 is achieved. The suspended material is filtered through Celit pad and washed with K2CO3 solution. The solution is diluted with EtOAc and washed with saturated K2CO3, brine and dried, filtered and concentrated to give crude product, which is purified by flash silica gel column, eluting with hexane (100%) gradient to hexane/ether (60/40%), to give the title intermediate as a solid (1.62 g, 53.1%).

後処理

  1. stirringstirring
  2. waitis continued for 20 minutes
  3. filtrationThe suspended material is filtered through Celit pad
  4. washwashed with K2CO3 solution
  5. additionThe solution is diluted with EtOAc
  6. washwashed with saturated K2CO3, brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give crude product, which
  11. customis purified by flash silica gel column
  12. washeluting with hexane (100%) gradient to hexane/ether (60/40%)

出典と根拠

ORDレコード
ord-4f82a12b8b6b4e0b823e207cd72b0dda
出典データセット
uspto-grants-2008_11
特許番号
US07449582B2

関連ノート

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