Water → 2-[4-(4-Chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamine

HRID 2240128Notes

Reaction equation

HRID 2240128 reaction equation
[N:1]([C:4]1[C:5]2[S:25][CH2:24][CH2:23][C:6]=2[N:7]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[N:9]=1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:8]3[N:9]=[C:4]([NH2:1])[C:5]4[S:25][CH2:24][CH2:23][C:6]=4[N:7]=3)[CH2:15][CH2:14]2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 866162804-Azido-2-[4-(4-chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 684421912-[4-(4-Chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamineYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.820 g (1.76 mmol) of 4-azido-2-[4-(4-chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidine (IV) is placed in 10 mL of tetrahydrofuran and 3.80 mL (3.80 mmol) of lithium aluminum hydride (1M solution in tetrahydrofuran) is slowly added dropwise. The reaction mixture is stirred for 4 hours at ambient temperature. Then 0.55 mL of 1N sodium hydroxide solution and 0.50 mL of water are added, the mixture is boiled for 0.3 hours, then cooled again. It is filtered, the filtrate is dried and evaporated to dryness. The residue is extracted with ethyl acetate and 1 N hydrochloric acid. The product precipitates out, is suction filtered, then extracted with ethyl acetate and 1 N sodium hydroxide solution. The organic phase is washed with water, dried, and evaporated to dryness. The residue is stirred with petroleum ether. 0.513 g of product V (84%) is obtained as a solid (m.p. 176-178° C.). 1H NMR (400 MHz, DMSO): 7.24 (2H, d); 6.98 (2H, d); 6.30 (2H, s); 3.77-3.68 (4H, m); 3.22 (2H, t); 3.17-3.09 (4H, m); 2.99 (2H, t).

Workup

  1. waitthe mixture is boiled for 0.3 hours
  2. temperaturecooled again
  3. filtrationIt is filtered
  4. customthe filtrate is dried
  5. customevaporated to dryness
  6. extractionThe residue is extracted with ethyl acetate and 1 N hydrochloric acid
  7. customThe product precipitates out
  8. filtrationfiltered
  9. extractionextracted with ethyl acetate and 1 N sodium hydroxide solution
  10. washThe organic phase is washed with water
  11. customdried
  12. customevaporated to dryness
  13. stirringThe residue is stirred with petroleum ether

Sources & evidence

ORD record
ord-761d63548aa24c31a67de18788b051e0
Source dataset
uspto-grants-2010_05
Patent number
US07723341B2

Reaction notes

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