Trifluoroacetic acid → 5-Chloro-3,4-dihydropyrido[2,3-D]pyrimidin-2(1H)-one

HRID 1045486

Reaction equation

[Cl:1][C:2]1[C:11]2[CH2:10][N:9](CC3C=CC(OC)=CC=3)[C:8](=[O:21])[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[C:11]2[CH2:10][NH:9][C:8](=[O:21])[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 669262915-chloro-3-[(4-methoxyphenyl)methyl]-1H,2H,3H,4H-pyrido[2,3-d]pyrimidin-2-one

Product 1

HCID 704982155-Chloro-3,4-dihydropyrido[2,3-D]pyrimidin-2(1H)-oneYield 101.7%

Conditions

Temperature: 80 °C

Procedure

1 (90 mg, 0.3 mmol) and TFA (2 mL) were added to a 5 mL sealed tube, and stirred overnight at 80° C. The TFA was removed, and the material was suspended in ether. The resulting precipitate was filtered to provide 3 (56 mg, 99% yield). LC-MS (M+H=184, obsd.=184). 1H NMR: (DMSO-D6) δ 4.37 (s, 2H); 7.03(d, 2H); 7.13 (s, 1H); 8.02 (d, 1H); 9.77 (s, 1H).

Workup

customsealed tube
customThe TFA was removed
filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record: ord-cb41e78705214a389700af2cb0e70cb8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569295B2

Linked notes

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