Potassium Carbonate → N2-Butyl-9-(4-chlorobutyl)-8-(methyloxy)-9H-purine-2,6-diamine

HRID 562715ノート

反応式

HRID 562715 の反応式
FC(F)(F)C(O)=O.[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][CH2:35][Cl:36]>CN(C=O)C>[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH2:33][CH2:34][CH2:35][Cl:36])=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178448879HCID 178448879、化合物

生成物 1

HCID 59252596N2-Butyl-9-(4-chlorobutyl)-8-(methyloxy)-9H-purine-2,6-diamine収率 109.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

N2-Butyl-8-(methyloxy)-9H-purine-2,6-diamine trifluoroacetate (5 g, 14.27 mmol) and potassium carbonate (4.93 g, 35.7 mmol) were suspended in DMF (40 ml) and heated to 50° C. under nitrogen for 30 mins. The mixture was cooled to room temperature, 1-bromo-4-chlorobutane (1.645 ml, 14.27 mmol) was added and stirring was continued at room temperature for 20 hours. The solvent was concentrated under vacuum and the residue was partitioned between DCM (100 ml) and water (100 ml). The layers were separated using a hydrophobic frit and the aqueous phase was re-extracted with DCM (100 ml). The combined organics extracts were concentrated in vacuo and the residue purified by chromatography using a FlashMaster apparatus (100 g silica cartridge) and using a DCM:methanol 0-25% gradient over 40 mins. The desired fractions were combined and concentrated under vacuum to give the impure title compound as a yellow oil (5.1 g).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationThe solvent was concentrated under vacuum
  3. customthe residue was partitioned between DCM (100 ml) and water (100 ml)
  4. customThe layers were separated
  5. extractionthe aqueous phase was re-extracted with DCM (100 ml)
  6. concentrationThe combined organics extracts were concentrated in vacuo
  7. customthe residue purified by chromatography
  8. waitmethanol 0-25% gradient over 40 mins
  9. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-1f4b6033fb3747debeccfb8c0ed5a7c1
出典データセット
uspto-grants-2011_11
特許番号
US08067426B2

反応ノート

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