Potassium Carbonate → N2-Butyl-9-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-8-methoxy-9H-purine-2,6-diamine

HRID 1010989ノート

反応式

HRID 1010989 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+].CS(O[CH2:36][CH:37]1[CH2:42][CH2:41][O:40][C:39]([CH3:44])([CH3:43])[CH2:38]1)(=O)=O.[Br-].[Li+]>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[CH2:36][CH:37]2[CH2:42][CH2:41][O:40][C:39]([CH3:44])([CH3:43])[CH2:38]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 82050Lithium BromideHCID 57699693(2,2-Dimethyltetrahydro-2H-pyran-4-yl)methyl methanesulfonateHCID 178448879HCID 178448879、化合物

生成物 1

HCID 57699692N2-Butyl-9-[(2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl]-8-methoxy-9H-purine-2,6-diamine収率 36.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of N2-Butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (200 mg) and potassium carbonate (236 mg) in dry DMF (2 mL) were heated at 60° C. under nitrogen with stirring for 1 h. (2,2-Dimethyltetrahydro-2H-pyran-4-yl)methyl methanesulfonate (152 mg) was added and stirring was continued for 5 h at 50° C. The reaction was cooled to room temperature and stirred for 16 h. Lithium bromide (50 mg) was added and heating was continued for 5 h at 50° C., then 8 h at 90° C. The mixture was quenched with water and extracted with EtOAc (×3). The combined organics were washed with water and brine, dried using a hydrophobic frit and evaporated to give crude material (210 mg). This was purified by C18 reverse phase chromatography (ISCO) using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluent (20-60%) to give the title compound (75 mg).

後処理

  1. additionwas added
  2. temperatureThe reaction was cooled to room temperature
  3. stirringstirred for 16 h
  4. temperatureheating
  5. waitwas continued for 5 h at 50° C.
  6. custom8 h
  7. customat 90° C
  8. customThe mixture was quenched with water
  9. extractionextracted with EtOAc (×3)
  10. washThe combined organics were washed with water and brine
  11. customdried
  12. customevaporated
  13. customto give crude material (210 mg)
  14. customThis was purified by C18 reverse phase chromatography (ISCO)

出典と根拠

ORDレコード
ord-65944a1b126141288cea51ab8e8f8cb4
出典データセット
uspto-grants-2011_07
特許番号
US07977344B2

反応ノート

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