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

HRID 547384Notes

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

Participants

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

customThe solvent was then removed under reduced pressure and to the residue
additionwas added MeOH
filtrationThe solid was filtered
washwashed with MeOH
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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