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Potassium Carbonate → 6-Amino-2-(butyloxy)-9-{4-[1-(1-ethylpropyl)-4-piperidinyl]butyl}-7,9-dihydro-8H-purin-8-one

HRID 1045017
ノート
印刷プレビュー

反応式

HRID 1045017 の反応式
Br[CH:2]([CH2:5][CH3:6])[CH2:3][CH3:4].[CH2:7]([O:11][C:12]1[N:20]=[C:19]2[C:15]([N:16]=[C:17]([O:31]C)[N:18]2[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[C:14]([NH2:33])[N:13]=1)[CH2:8][CH2:9][CH3:10].CCN(C(C)C)C(C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CS(C)=O>[NH2:33][C:14]1[N:13]=[C:12]([O:11][CH2:7][CH2:8][CH2:9][CH3:10])[N:20]=[C:19]2[C:15]=1[NH:16][C:17](=[O:31])[N:18]2[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][N:28]([CH:2]([CH2:5][CH3:6])[CH2:3][CH3:4])[CH2:27][CH2:26]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 157383-Bromopentane2 回HCID 81531Diisopropylethylamine2 回HCID 583062222-(Butyloxy)-8-(methyloxy)-9-[4-(4-piperidinyl)butyl]-9H-purin-6-amine

生成物 1

HCID 672336886-Amino-2-(butyloxy)-9-{4-[1-(1-ethylpropyl)-4-piperidinyl]butyl}-7,9-dihydro-8H-purin-8-one収率 13.6%

試薬・触媒・溶媒

2
HCID 679Dimethyl Sulfoxide溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

3-Bromopentane (0.1 mmol) was weighed into a tube and an aliquot (0.4 ml, 0.12 mmol) of a solution of 2-(butyloxy)-8-(methyloxy)-9-[4-(4-piperidinyl)butyl]-9H-purin-6-amine (0.452 g mg, 1.2 mmol) suspended in DMF (4.8 ml) was added. DIPEA (40 μl, 0.229 mmol) was added and heated at 50° C. for 18 hours. An additional portion of 3-bromopentane (15 μl) and DIPEA (40 μl) was added and heating continued for a further 18 hours. Potassium carbonate (46 mg) was added and heating continued for a further 72 hours. DMSO (200 uL) was added and the resultant mixture filtered, the solution was purified by Mass Directed AutoPrep (Method A). The solvent was evaporated in vacuo using the Genevac. The residue was redissolved in 4M HCl/dioxane (0.2 ml), capped and stood at room temperature for 18 hours. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus. The sample was dissolved in 1:1 DMSO:MeOH and purified by MDAP (Method C) and the solvent was evaporated in vacuo using the Genevac. The material was redissolved in methanol (0.5 ml), and applied to a 0.1 g aminopropyl SPE (preconditioned with methanol, 1.5 ml). The cartridge was eluted with methanol (1.5 ml), the solvent was removed to give the title compound (5.9 mg).

後処理

  1. additionwas added
  2. temperatureheating
  3. temperatureheating
  4. waitcontinued for a further 72 hours
  5. filtrationthe resultant mixture filtered
  6. customthe solution was purified by Mass Directed AutoPrep (Method A)
  7. customThe solvent was evaporated in vacuo
  8. dissolutionThe residue was redissolved in 4M HCl/dioxane (0.2 ml)
  9. customcapped
  10. waitstood at room temperature for 18 hours
  11. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
  12. dissolutionThe sample was dissolved in 1:1 DMSO
  13. customMeOH and purified by MDAP (Method C)
  14. customthe solvent was evaporated in vacuo
  15. dissolutionThe material was redissolved in methanol (0.5 ml)
  16. washThe cartridge was eluted with methanol (1.5 ml)
  17. customthe solvent was removed

出典と根拠

ORDレコード
ord-d4d42584fddf48059a1d88b22ce4f254
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08563717B2

反応ノート

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