Potassium Acetate → HCID 66611486、化合物

HRID 1621453

反応式

HRID 1621453 の反応式
Cl[C:2]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.[O:18]1[CH2:22][CH2:21][O:20][CH:19]1[C:23]1[CH:24]=[C:25](B(O)O)[C:26]([F:29])=[N:27][CH:28]=1.C([O-])(=O)C.[K+]>CCO.C(P([Pd](P(C1C=CC(N(C)C)=CC=1)(C(C)(C)C)C(C)(C)C)(Cl)Cl)(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)(C)C>[O:18]1[CH2:22][CH2:21][O:20][CH:19]1[C:23]1[CH:24]=[C:25]([C:2]2[N:10]=[C:9]([CH3:11])[N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[C:26]([F:29])=[N:27][CH:28]=1

参加物

6

反応物 3

HCID 517044Potassium AcetateHCID 595482686-chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 595483675-(1,3-Dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid

生成物 1

HCID 66611486HCID 66611486、化合物収率 93.4%

試薬・触媒・溶媒 2

HCID 178482906HCID 178482906、化合物触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

6-Chloro-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (3.200 g, 12.66 mmol), 5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-ylboronic acid (3.165 g, 14.86 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphino)dichloropalladium (514.9 mg, 0.7272 mmol), and potassium acetate (4.180 g, 42.59 mmol) were suspended in EtOH (50 mL) and water (10 mL) and nitrogen was bubbled through the suspension for about 15 seconds. Then, the flask was fitted with a reflux condenser and placed in a preheated oil bath (80° C.), and stirred under nitrogen for 1 hour. The reaction was cooled to room temperature, poured into water (125 mL), and extracted with DCM. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter (600 mL fritted filter with about 3 inches of silica gel, 40:1 DCM/2N ammonia in MeOH). The fractions with product were collected, concentrated, and washed repeatedly with hexanes and dried to give 6-(5-(1,3-dioxolan-2-yl)-2-fluoropyridin-3-yl)-2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (4.557 g), which was used for the next step. MS (ESI pos. ion) m/z 386 (M+H)+.

後処理

  1. customwater (10 mL) and nitrogen was bubbled through the suspension for about 15 seconds
  2. customThen, the flask was fitted with a reflux condenser
  3. customplaced in a preheated oil bath
  4. temperatureThe reaction was cooled to room temperature
  5. additionpoured into water (125 mL)
  6. extractionextracted with DCM
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified on a silica gel
  11. filtrationfilter (600 mL fritted filter with about 3 inches of silica gel, 40:1 DCM/2N ammonia in MeOH)
  12. customThe fractions with product were collected
  13. concentrationconcentrated
  14. washwashed repeatedly with hexanes
  15. customdried

出典と根拠

ORDレコード
ord-57380d7b9b594c1f869e802df09f437a
出典データセット
uspto-grants-2014_07
特許番号
US08772480B2

関連ノート

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