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

HRID 1788029Notes

Reaction equation

HRID 1788029 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 86616280HCID 86616280, compound

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-a40edab6a1d04ea8a582a62d45eb99e5
Source dataset
uspto-grants-2009_03
Patent number
US07511045B2

Reaction notes

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