Triphenylphosphine → 1-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

HRID 432129ノート

反応式

HRID 432129 の反応式
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[Cl:11])[NH:4][N:3]=1.[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22](O)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([N:4]2[C:5]3=[N:6][CH:7]=[N:8][C:9]([Cl:11])=[C:10]3[C:2]([Br:1])=[N:3]2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 784611-Benzylpiperidin-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1784783943-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine2 回

生成物 1

HCID 223471731-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine収率 121.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (Intermediate B) (5.0 g, 21.42 mmol), 1-benzyl-4-piperidinol (8.2 g, 42.83 mmol) and triphenylphosphine (11.23 g, 42.83 mmol)were suspended in 250 ml of tetrahydrofuran. The reaction mixture was cooled in an ice-water bath and diethyl azodicarboxylate (6.8 ml, 42.83 mmol) was added dropwise. 10 minutes later, the reaction mixture was allowed to warm up to room temperature. After stirring for 2 hours, solvent was removed and the residue was taking into ethyl acetate. The organic layer was washed, dried and evaporated. The crude product was passed through Biotage flash column using dichloromethane/ethyl acetate (90:10) as the mobile phase to yield 10.56 g of 1-(1-benzyl-4-piperidinyl)-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine. The product was 61% pure with a HPLC retention time of 12.46 min. (HPLC condition: 5 to 95% CH3CN in 0.1 N aqueous ammonium acetate over 20 min., the column size is 3.9×150 mm, 300 A).

後処理

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. custom10 minutes
  3. customsolvent was removed
  4. washThe organic layer was washed
  5. customdried
  6. customevaporated

出典と根拠

ORDレコード
ord-85d2c391e47f4a7baa6eadffbdce2027
出典データセット
uspto-grants-2003_12
特許番号
US06660744B1

反応ノート

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