Phenyl isocyanate → (2-Piperazin-1-yl-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamine

HRID 1805980ノート

反応式

HRID 1805980 の反応式
C1(N[C:8]2[C:9]3[S:33][CH2:32][CH2:31][C:10]=3[N:11]=[C:12]([N:14]3[CH2:19][CH2:18][N:17](C4C=CC(C(OCC)=O)=CC=4)[CH2:16][CH2:15]3)[N:13]=2)CCCCC1.[C:34]1([N:40]=C=O)C=CC=[CH:36][CH:35]=1>O1CCCC1>[N:14]1([C:12]2[N:13]=[C:8]([CH2:36][CH2:35][CH2:34][NH2:40])[C:9]3[S:33][CH2:32][CH2:31][C:10]=3[N:11]=2)[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1

参加物

4

反応物 2

HCID 7672Phenyl isocyanateHCID 86616266Ethyl 4-[4-(4-cyclohexylamino-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]benzoate

生成物 1

HCID 68438559(2-Piperazin-1-yl-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamine収率 85.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.330 g (1.0 mmol) of cyclohexyl-(2-piperazin-1-yl-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)-amine (VI) and 0.115 mL (1.0 mmol) of phenyl isocyanate are placed in 12.5 mL of tetrahydrofuran, then stirred for 1 hour at ambient temperature. Then the reaction mixture is concentrated by evaporation. The residue is stirred with water, suction filtered, washed with water and petroleum ether, then dried. The crude product is purified by chromatography through a 25 g silica gel cartridge with a solvent mixture of petroleum ether/ethyl acetate 1/1. 0.240 g of product VII (53%) is obtained as a powder (m.p. 207-210° C.). 1H NMR (400 MHz, DMSO): 8.51 (1H, s); 7.47 (2H, d); 7.23 (2H, t); 6.92 (1H, t); 6.11 (1H, d); 3.91-3.78 (1H, m); 3.69-3.59 (4H, m); 3.53-3.44 (4H, m); 3.22 (2H, t); 2.98 (2H, t); 1.92-1.78 (2H, m); 1.79-1.67 (2H, m); 1.65-1.56 (1H, m); 1.37-1.21 (4H, m); 1.18-1.04 (1H, m).

後処理

  1. concentrationThen the reaction mixture is concentrated by evaporation
  2. stirringThe residue is stirred with water, suction
  3. filtrationfiltered
  4. washwashed with water and petroleum ether
  5. customdried
  6. customThe crude product is purified by chromatography through a 25 g silica gel cartridge with a solvent mixture of petroleum ether/ethyl acetate 1/1

出典と根拠

ORDレコード
ord-6a41b258d6474750b0c9dafece088fe7
出典データセット
uspto-grants-2013_01
特許番号
US08354531B2

反応ノート

読み込み中…