Sodium Chlorite → 4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carboxylic acid

HRID 400566ノート

反応式

HRID 400566 の反応式
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([C:10]2[CH:11]=[C:12]([CH:15]=[O:16])[O:13][CH:14]=2)=[N:3][CH:2]=1.P([O-])(O)(O)=[O:18].[Na+].Cl([O-])=O.[Na+]>CS(C)=O.O>[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([C:10]2[CH:11]=[C:12]([C:15]([OH:18])=[O:16])[O:13][CH:14]=2)=[N:3][CH:2]=1

参加物

6

反応物 3

HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 576473994-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbaldehyde

生成物 1

HCID 576474134-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carboxylic acid収率 64.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒3 回

実験手順

600 mg [2.82 mMols] of 4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbaldehyde was dissolved in 5.0 mL of DMSO/2.0 mL of water and stirred with 210 mg [1.75 mMols] of sodium dihydrogen phosphate, reducing the temperature as cold as possible so as not to effect crystallization. 532 mg sodium chlorite [5.88 mMols] in 4.0 mL of water was slowly added dropwise to this stirring solution. Solution was allowed to warm to ambient temperature and diluted with water to effect precipitation. The fine flocculent material was centrifuged down and washed with water and re-centrifuged. The oily pellet was transferred to a RB with acetonitrile and the solvents were removed under reduced pressure. The residue was stirred with a mixture of MTBE/acetonitrile (4:1) overnight and the powder isolated in the morning via suction filtration, washed with the same mixture and air dried. The material, (yield 64.6%) a beige powder, was utilized without further purification. LC/MS m+1 230/m−1 228.

後処理

  1. customcrystallization
  2. customprecipitation
  3. washwashed with water
  4. customthe solvents were removed under reduced pressure
  5. customthe powder isolated in the morning via suction filtration
  6. washwashed with the same mixture and air
  7. customdried

出典と根拠

ORDレコード
ord-efe8b6c7aa3644a09102554290a76edc
出典データセット
uspto-grants-2014_06
特許番号
US08741912B2

反応ノート

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