2-(3-Hydroxypiperidino)-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4H-pyrido[1,2-a]pyrimidin-4-one → tert-Butyl (E)-3-{2-[(3R)-3-Formyloxyhexahydro-1-pyridinyl]-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

HRID 1828494Notes

Reaction equation

HRID 1828494 reaction equation
OC1N=C2C=C(/C=C/C3SC=C(C(C)C)N=3)C=CN2C(=O)C=1.OC1CCCN(C2N=C3C=C(/C=C/C4SC=C(C(C)C)N=4)C=CN3C(=O)C=2)C1.[CH:51]([O:53][CH:54]1[CH2:59][CH2:58][CH2:57][N:56]([C:60]2[N:61]=[C:62]3[CH:79]=[C:78](/[CH:80]=[CH:81]/[C:82]4[S:83][CH:84]=[C:85]([CH:87]([CH3:89])[CH3:88])[N:86]=4)[CH:77]=[CH:76][N:63]3[C:64](=[O:75])[C:65]=2/[CH:66]=[CH:67]/[C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[CH2:55]1)=[O:52]>>[CH:51]([O:53][C@@H:54]1[CH2:59][CH2:58][CH2:57][N:56]([C:60]2[N:61]=[C:62]3[CH:79]=[C:78](/[CH:80]=[CH:81]/[C:82]4[S:83][CH:84]=[C:85]([CH:87]([CH3:89])[CH3:88])[N:86]=4)[CH:77]=[CH:76][N:63]3[C:64](=[O:75])[C:65]=2/[CH:66]=[CH:67]/[C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[CH2:55]1)=[O:52]

Participants

4

Reactant 3

HCID 865881182-(3-Hydroxypiperidino)-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 86588120tert-Butyl (E)-3-{2-(3-formyloxypiperidino)-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoateHCID 1363468402-Hydroxy-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 86588125tert-Butyl (E)-3-{2-[(3R)-3-Formyloxyhexahydro-1-pyridinyl]-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoateYield 56%

Procedure

2-Hydroxy-8-[(E)-2-(4-isopropyl-1,3-thiazol-2-yl)-1-ethenyl]-4H-pyrido[1,2-a]-pyrimidin-4-one (500 mg, 1.60 mmol) was treated in the same manner as in Example 102, (F) and (G) to obtain the title compound (488 mg, 56%).

Sources & evidence

ORD record
ord-bdb41ef4385449cb859153b216327a87
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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