tert-Butyl (E)-3-{2-(3-hydroxypiperidino)-8-[(4-isopropyl-1,3-thiazol-2-yl)-methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate → (E)-3-{8-[2-(4-Ethyl-2-thienyl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]-pyrimidin-3-yl}-2-propenoic acid

HRID 1828439Notes

Reaction equation

OC1CCCN(C2N=C3C=C(OCC4SC=C(C(C)C)N=4)C=CN3C(=O)C=2/C=C/C(OC(C)(C)C)=O)C1.[CH2:38]([C:40]1[CH:41]=[C:42]([CH2:45][CH2:46][C:47]2[CH:72]=[CH:71][N:50]3[C:51](=[O:70])[C:52](/[CH:61]=[CH:62]/[C:63]([O:65]C(C)(C)C)=[O:64])=[C:53]([N:55]4[CH2:60][CH2:59][O:58][CH2:57][CH2:56]4)[N:54]=[C:49]3[CH:48]=2)[S:43][CH:44]=1)[CH3:39]>>[CH2:38]([C:40]1[CH:41]=[C:42]([CH2:45][CH2:46][C:47]2[CH:72]=[CH:71][N:50]3[C:51](=[O:70])[C:52](/[CH:61]=[CH:62]/[C:63]([OH:65])=[O:64])=[C:53]([N:55]4[CH2:60][CH2:59][O:58][CH2:57][CH2:56]4)[N:54]=[C:49]3[CH:48]=2)[S:43][CH:44]=1)[CH3:39]

Participants

Reactant 2

HCID 86588098tert-Butyl (E)-3-{2-(3-hydroxypiperidino)-8-[(4-isopropyl-1,3-thiazol-2-yl)-methoxy]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

HCID 86588099tert-butyl (E)-3-{8-[2-(4-ethyl-2-thienyl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]-pyrimidin-3-yl}-2-propenoate

Product 1

HCID 22063594(E)-3-{8-[2-(4-Ethyl-2-thienyl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]-pyrimidin-3-yl}-2-propenoic acidYield 56%

Procedure

Reactions were performed in the same manner as in Example 1, (L) by using tert-butyl (E)-3-{8-[2-(4-ethyl-2-thienyl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]-pyrimidin-3-yl}-2-propenoate (65 mg, 0.13 mmol) as a starting material. As a result, 32 mg (56%) of yellow crystals were obtained.

Sources & evidence

ORD record: ord-c82de4425493470b8cb699aea9f85abc
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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