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p-Toluenesulfonic acid → Methyl 9-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-oxo-4-H-pyrido[1,2-a]pyrimidine-2-carboxylate

HRID 547384
Notes
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Reaction equation

HRID 547384 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=[CH:4][N+:3]=1[O-].[CH3:20][O:21][C:22]([C:24]#[C:25][C:26]([O:28]C)=O)=[O:23].C1(C)C=CC(S(O)(=O)=[O:37])=CC=1>C(Cl)(Cl)Cl>[CH2:11]([O:10][C:9]([NH:8][C:7]1[C:2]2=[N:1][C:24]([C:22]([O:21][CH3:20])=[O:23])=[C:25]([OH:37])[C:26](=[O:28])[N:3]2[CH:4]=[CH:5][CH:6]=1)=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12980Dimethyl acetylenedicarboxylateHCID 178508042HCID 178508042, compound

Product 1

HCID 54751204Methyl 9-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-oxo-4-H-pyrido[1,2-a]pyrimidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of benzyl (2-amino-1-oxidopyridin-3-yl)carbamate in chloroform (filtered over alumina) was added DMAD and p-toluenesulfonic acid. The suspension was stirred at 70° C. for 12 hours. The solvent was then removed under reduced pressure and to the residue was added MeOH. The solid was filtered, washed with MeOH and dried under vacuum.

Workup

  1. customThe solvent was then removed under reduced pressure and to the residue
  2. additionwas added MeOH
  3. filtrationThe solid was filtered
  4. washwashed with MeOH
  5. customdried under vacuum

Sources & evidence

ORD record
ord-a538fd7e89ea4122a0ef860d60e13e5c
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07939537B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes