Citric Acid → tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

HRID 1476614Notes

Reaction equation

HRID 1476614 reaction equation
CO[C:3]([C:5]1[S:6][C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][C:9]=1[NH:10][C:11]([NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=[O:12])=[O:4].C[O-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[O:12]=[C:11]1[NH:10][C:9]2[CH:8]=[C:7]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[S:6][C:5]=2[C:3](=[O:4])[N:13]1[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 10942334Sodium MethoxideHCID 67258244HCID 67258244, compound

Product 1

HCID 67257815tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-({[2-(methoxycarbonyl)-5-phenyl-3-thienyl]carbamoyl}amino)piperidine-1-carboxylate (2.00 g; compound B51) in MeOH (20 ml) is added sodium methoxide (300 mg) in three portions at RT. The reaction mixture is refluxed for 3 d and then allowed to come to RT. Ice cold water (30 ml) is added and the pH is adjusted to 4 by addition of citric acid. The resulting suspension is stirred for 2 h at RT; then the precipitate is filtered off, washed with water and dried in vacuo at 50° C. The crude title compound is taken up in MeOH (25 ml) and refluxed for 3 h. The hot suspension is filtered, and the filter cake is washed with hot MeOH three times and dried in vacuo at 45° C. to afford the title compound as a solid.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 d
  2. customto come to RT
  3. filtrationthen the precipitate is filtered off
  4. washwashed with water
  5. customdried in vacuo at 50° C
  6. temperaturerefluxed for 3 h
  7. filtrationThe hot suspension is filtered
  8. washthe filter cake is washed with hot MeOH three times
  9. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-c961f0e94dd243d5b9b68aa077ee84fe
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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