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

HRID 1805980노트

반응식

HRID 1805980 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6a41b258d6474750b0c9dafece088fe7
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354531B2

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