Potassium Carbonate → 3-Bromopentane

HRID 2403909ノート

反応式

HRID 2403909 の反応式
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:23]C)[N:12]2[CH2:15][CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]2)=[C:8]([NH2:25])[N:7]=1)[CH2:2][CH2:3][CH3:4].CCN(C(C)C)C(C)C.C(=O)([O-])[O-].[K+].[K+].[Br:41][CH:42]([CH2:45][CH3:46])[CH2:43][CH3:44]>C(#N)C.CN(C=O)C.CO.CS(C)=O>[Br:41][CH:42]([CH2:45][CH3:46])[CH2:43][CH3:44].[NH2:25][C:8]1[N:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:23])[N:12]2[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][N:19]([CH:42]([CH2:45][CH3:46])[CH2:43][CH3:44])[CH2:18]1

参加物

10

反応物 4

HCID 11430Potassium CarbonateHCID 157383-BromopentaneHCID 81531Diisopropylethylamine2 回HCID 583062622-(Butyloxy)-8-(methyloxy)-9-[2-(3-piperidinyl)ethyl]-9H-purin-6-amine

生成物 2

HCID 157383-BromopentaneHCID 672333456-Amino-2-(butyloxy)-9-{2-[1-(1-ethylpropyl)-3-piperidinyl]ethyl}-7,9-dihydro-8H-purin-8-one

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒2 回

反応条件

温度
50 °C

実験手順

A solution of 3-bromopentane was prepared by dissolving 1 mmole in acetonitrile (1 ml). A portion of this solution (0.12 ml, equivalent to 0.12 mmol) was added to a test tube. 2-(Butyloxy)-8-(methyloxy)-9-[2-(3-piperidinyl)ethyl]-9H-purin-6-amine (435 mg, 1.2 mmol) was dissolved in DMF (6.0 ml) and an aliquot (0.5 ml, 0.1 mmol) dispensed to the tube. DIPEA (40 μL, 0.23 mmol) and potassium carbonate (46 mg, 0.3 mmol) added, and heated to 50° C. for 18 hr. An additional aliquot of 3-bromopentane in acetonitrile (80 uL, 0.08 mmol) (total added 0.2 mmol) and DIPEA (40 uL, 0.23 mmol) was added and continued stirring with heat at 50° C. for a further 18 hours. DMSO:MeOH (200 uL) was added, the mixture filtered and purified by Mass Directed AutoPrep (Method A). The solvent was evaporated in vacuo using the Genevac. The residue was redissolved in a solution of 4M HCl/dioxane (0.2 ml) and allowed to stand at room temperature for 4 hours. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus. The material was redissolved in methanol (0.5 ml) and applied to an aminopropyl SPE (0.1 g, 3 ml, preconditioned in methanol (1.5 ml)). The product was eluted with additional methanol (1.5 ml). The solvent was removed to give the title compound (6 mg).

後処理

  1. additionA portion of this solution (0.12 ml, equivalent to 0.12 mmol) was added to a test tube
  2. temperaturewith heat at 50° C. for a further 18 hours
  3. filtrationthe mixture filtered
  4. custompurified by Mass Directed AutoPrep (Method A)
  5. customThe solvent was evaporated in vacuo
  6. dissolutionThe residue was redissolved in a solution of 4M HCl/dioxane (0.2 ml)
  7. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
  8. dissolutionThe material was redissolved in methanol (0.5 ml)
  9. washThe product was eluted with additional methanol (1.5 ml)
  10. customThe solvent was removed

出典と根拠

ORDレコード
ord-8d9be9b149b143fab21f4c31f508b6f6
出典データセット
uspto-grants-2014_08
特許番号
US08802684B2

反応ノート

読み込み中…