Potassium Carbonate → 6-chloro-2-methyl-7H-purine

HRID 1604766ノート

反応式

HRID 1604766 の反応式
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[C:11](=O)([O-])[O-].[K+].[K+]>C1(=O)OC(C)CO1>[CH3:11][C:9]1[N:8]=[C:7]2[C:3]([NH:4][CH:5]=[N:6]2)=[C:2]([Cl:1])[N:10]=1

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 53592776-Chloropurine

生成物 1

HCID 54089976-chloro-2-methyl-7H-purine

試薬・触媒・溶媒 1

HCID 7924Propylene Carbonate溶媒

実験手順

6-Chloropurine (dried over phosphorus pentoxide, 1.13 g), MBTG (3.87 g) and freshly-dried potassium carbonate (1.5 g) are stirred in anhydrous propylene carbonate (30 ml) at room temperature for 24 hours. The dark mixture is filtered and purified by column chromatography over silica 100 g) eluting with a 0-80% gradient of ethyl acetate in chloroform. The main fraction (other than unreacted 6-chlorpurine) is dried and recrystallized from boiling ethanol to yield methyl 6-chloropurine-9-(2',3',4'-tri-O-acetyl-β-D-glucopyranuronate (312 mg) and benzylamine (171 μl) are heated together in 1-butanol (13.5 ml) at 100° C. for 1 hour. The solid dissolves readily to give a clear yellow solution. Most of the butanol is removed under vacuum to yield a whitish solid which is shaken with 5% sodium hydroxide in 50% aqueous ethanol (25 ml) for 1-2 hours at room temperature. After neutralization, the product is dried under vacuum to remove traces of butanol. Crude BA9GN sodium salt is then purified by reverse-phase chromatography as in Method 1.

後処理

  1. filtrationThe dark mixture is filtered
  2. custompurified by column chromatography over silica 100 g)
  3. washeluting with a 0-80% gradient of ethyl acetate in chloroform
  4. dry with materialThe main fraction (other than unreacted 6-chlorpurine) is dried
  5. customrecrystallized

出典と根拠

ORDレコード
ord-71a4a81d0ef542fab0a66784d9bd52a1
出典データセット
uspto-grants-1999_11
特許番号
US05994629

反応ノート

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