tert-Butyl piperazine-1-carboxylate → HCID 20068695, compound

HRID 982135Notes

Reaction equation

HRID 982135 reaction equation
[Cl:1][C:2]1[C:3]2[S:14][CH2:13][CH2:12][CH2:11][C:4]=2[N:5]=[C:6]([CH:8]([CH3:10])[CH3:9])[N:7]=1.C(OC([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=O)(C)(C)C>C(O)CC(C)C>[ClH:1].[ClH:1].[CH3:9][CH:8]([C:6]1[N:7]=[C:2]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:3]2[S:14][CH2:13][CH2:12][CH2:11][C:4]=2[N:5]=1)[CH3:10]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 15055709HCID 15055709, compound

Product 1

HCID 20068695HCID 20068695, compound

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A solution of 4-chloro-7,8-dihydro-2-(1-methylethyl)-6H-thiopyrano[3,2-d]pyrimidine (from Table I) (2.8 g) and N-tert-butoxycarbonylpiperazine (5.0 g) in isoamyl alcohol (50 ml) was heated at reflux for 1 hour, cooled, filtered and the solvent distilled at reduced pressure. The residue was dissolved in ether, washed with H2O and brine, dried over magnesium sulfate and evaporated in vacuo. To the residue was added trifluoroacetic acid (40 ml) which after 1 hour was distilled at reduced pressure. The residue was treated with ice and excess 10N sodium hydroxide, extracted into CH2Cl2, washed with water and brine and dried over K2CO3. The CH2Cl2 was distilled at reduced pressure and the residue was dissolved in ethanol (30 ml), treated with 10N ethanolic HCl (3 ml) and ether (30 ml) to give the title compound which melts at 256° to 258° C. after recrystallization from 2-propanol-ether.

Workup

  1. temperatureat reflux for 1 hour
  2. temperaturecooled
  3. filtrationfiltered
  4. distillationthe solvent distilled at reduced pressure
  5. dissolutionThe residue was dissolved in ether
  6. washwashed with H2O and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. additionTo the residue was added trifluoroacetic acid (40 ml) which after 1 hour
  10. distillationwas distilled at reduced pressure
  11. additionThe residue was treated with ice and excess 10N sodium hydroxide
  12. extractionextracted into CH2Cl2
  13. washwashed with water and brine
  14. dry with materialdried over K2CO3
  15. distillationThe CH2Cl2 was distilled at reduced pressure
  16. dissolutionthe residue was dissolved in ethanol (30 ml)
  17. additiontreated with 10N ethanolic HCl (3 ml) and ether (30 ml)

Sources & evidence

ORD record
ord-5a04a65e9eed41778fb685588af2670a
Source dataset
uspto-grants-1991_02
Patent number
US04994464

Reaction notes

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