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

HRID 1805980Notes

Reaction equation

HRID 1805980 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6a41b258d6474750b0c9dafece088fe7
Source dataset
uspto-grants-2013_01
Patent number
US08354531B2

Reaction notes

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