HCID 118875884, compound → 3-(1-methyl-2,4-dioxo-6-(3-(trifluoromethyl)phenoxy)-5-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate

HRID 60457Notes

Reaction equation

O[CH:2]([C:37]1[CH:38]=[N:39][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:41][CH:42]=1)[C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][CH2:15][CH2:16][O:17][CH:18]3CCCC[O:19]3)[C:9](=[O:24])[N:8]([CH3:25])[C:7]=2[N:6]=[CH:5][C:4]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1>C(O)=O.[Zn]>[CH:18]([O:17][CH2:16][CH2:15][CH2:14][N:10]1[C:11](=[O:13])[C:12]2[C:3]([CH2:2][C:37]3[CH:38]=[N:39][C:40]([C:43]([F:46])([F:44])[F:45])=[CH:41][CH:42]=3)=[C:4]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:35])([F:34])[F:36])[CH:28]=3)[CH:5]=[N:6][C:7]=2[N:8]([CH3:25])[C:9]1=[O:24])=[O:19]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-(hydroxy(6-(trifluoromethyl)pyridin-3-yl)methyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethyl)phenoxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (See Compound 32, step 2, 75 mg, 0.114 mmol) in HCOOH (3 mL) was added Zn dust (37.5 mg, 0.573 mmol). The reaction was heated at 50° C. for 2 h, cooled to RT and filtered. The filtrate was concentrated and dried to give 3-(1-methyl-2,4-dioxo-6-(3-(trifluoromethyl)phenoxy)-5-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (35 mg, 52.4% yield) as a solid. LCMS: MH+ 583 and TR=1.979 min.

Workup

temperaturecooled to RT
filtrationfiltered
concentrationThe filtrate was concentrated
customdried

Sources & evidence

ORD record: ord-1351072edf2c43ff805e42f86f8f6c53
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440972B2

Reaction notes

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