Potassium Carbonate → N2-Butyl-8-(methyloxy)-9-[2-[(3R)-tetrahydro-3-furanyl]ethyl}-9H-Purine-2,6-diamine

HRID 1011079ノート

反応式

HRID 1011079 の反応式
[CH2:1]([NH:5][C:6]1[NH:14][C:13]2[C:9]([N:10]=[C:11]([O:15][CH3:16])[N:12]=2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][C@@H:27]1[CH2:31][CH2:30][O:29][CH2:28]1>CN(C=O)C>[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:15][CH3:16])[N:12]2[CH2:25][CH2:26][C@@H:27]2[CH2:31][CH2:30][O:29][CH2:28]2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 52324314(3S)-3-(2-bromoethyl)oxolaneHCID 178448876HCID 178448876、化合物

生成物 1

HCID 57699833N2-Butyl-8-(methyloxy)-9-[2-[(3R)-tetrahydro-3-furanyl]ethyl}-9H-Purine-2,6-diamine収率 79.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

N2-Butyl-8-(methyloxy)-3H-purine-2,6-diamine (157 mg, 0.447 mmol) was heated in dry DMF (3 ml) with potassium carbonate (232 mg, 1.675 mmol) at 60° C. for one hour. (3S)-3-(2-Bromoethyl)tetrahydrofuran (100 mg, 0.558 mmol) in dry DMF (2 ml) was added and the mixture stirred and heated to 60° C. under nitrogen for 4 hours. The mixture was cooled to room temperature, quenched into water (40 ml) and extracted with ethyl acetate (3×25 ml). The organic extracts were combined, dried by passage through a hydrophobic frit and concentrated under vacuum. The residue was dissolved in 1:1 MeOH:DMSO and purified by mass directed autopreparation. The desired fractions were combined and concentrated using a nitrogen blowdown unit to give the title compound as a white solid (119 mg).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched into water (40 ml)
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. customdried by passage through a hydrophobic frit
  5. concentrationconcentrated under vacuum
  6. dissolutionThe residue was dissolved in 1:1 MeOH
  7. customDMSO and purified by mass
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-50c59ce09a894f1e973595b425e41c72
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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