Sodium Carbonate → 3-phenyl-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 432484ノート

反応式

HRID 432484 の反応式
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:31]1([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[N:8][C:9]=3[NH2:11])[N:4]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:3]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 223468963-iodo-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

生成物 1

HCID 223469183-phenyl-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-4-amine収率 45.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A solution of 3-iodo-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1.0 g, 1.99 mmol) in dimethylformamide (20 mL) was treated with phenylboronic acid (0.485 g, 3.8 mmol), tetrakis(triphenylphosphine)palladium (0.138 g, 0.119 mmol), and a solution of sodium carbonate (0.506 g, 4.78 mmol) in water (10 mL). The reaction mixture was stirred at 80° C. for 18.5 h under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and water (15 mL) was added. The precipitate was filtered and was washed with water. The crude solid was triturated with diethyl ether (30 mL). The resulting solid was dried over night on the lyophilizer to give 0.407 g (45%) of 3-phenyl-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-4-amine. 1H NMR (DMSO-d6, 400 MHz) δ 7.9416 (s, 1H), 7.6190-7.6011 (m, 2H), 7.5369-7.4493 (m, 3H), 7.3995-7.2248 (m, 15H); HPLC Waters 2690 Alliance HPLC (Symmetry Shield RP18 3.5 μm, 2.1×50 mm; 5%-95% acetonitrile-0.1 M ammonium acetate over 15 min, 0.5 mL/min) Rt =11.813 min (97%).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe precipitate was filtered
  3. washwas washed with water
  4. customThe crude solid was triturated with diethyl ether (30 mL)
  5. customThe resulting solid was dried over night on the lyophilizer

出典と根拠

ORDレコード
ord-dc6d5a786f8943d0b029f857d2af4d14
出典データセット
uspto-grants-2003_12
特許番号
US06660744B1

反応ノート

読み込み中…