tert-Butyl (E)-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-2-(tetrahydro-3-furanylmethoxy)-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate → (E)-3-{8-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-2-(tetrahydro-3-furanylmethoxy)-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoic acid

HRID 1828506Notes

Reaction equation

HRID 1828506 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:37]=[CH:36][N:14]3[C:15](=[O:35])[C:16](/[CH:26]=[CH:27]/[C:28]([O:30]C(C)(C)C)=[O:29])=[C:17]([O:19][CH2:20][CH:21]4[CH2:25][CH2:24][O:23][CH2:22]4)[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]>C(Cl)Cl.C(O)=O>[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:37]=[CH:36][N:14]3[C:15](=[O:35])[C:16](/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29])=[C:17]([O:19][CH2:20][CH:21]4[CH2:25][CH2:24][O:23][CH2:22]4)[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86588137tert-Butyl (E)-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-2-(tetrahydro-3-furanylmethoxy)-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate2×

Product 1

HCID 22063562(E)-3-{8-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-2-(tetrahydro-3-furanylmethoxy)-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoic acidYield 156.7%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

The tert-butyl (E)-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-2-(tetrahydro-3-furanylmethoxy)-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate (10 mg) obtained in (A) was dissolved in methylene chloride (1 ml) and formic acid (1 ml), and then the mixture was stirred for 5 hours. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography to obtain the title compound (14 mg).

Workup

  1. customAfter the solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-26a6484b59044c70bb5e7d631c283be8
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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