HCID 118875496, compound → HCID 118875899, compound

HRID 60474Notes

Reaction equation

[Cl:1][C:2]1[CH:40]=[CH:39][C:5]([O:6][C:7]2[CH:29]=[N:28][C:10]3[N:11]([CH3:27])[C:12](=[O:26])[N:13]([CH2:16][CH2:17][CH2:18][O:19][CH:20]4CCCC[O:21]4)[C:14](=[O:15])[C:9]=3[C:8]=2[CH:30]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)O)=[CH:4][CH:3]=1>C(O)=O.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:29]=[N:28][C:10]3[N:11]([CH3:27])[C:12](=[O:26])[N:13]([CH2:16][CH2:17][CH2:18][O:19][CH:20]=[O:21])[C:14](=[O:15])[C:9]=3[C:8]=2[CH2:30][C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)=[CH:39][CH:40]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 6-(4-chlorophenoxy)-5-((4-fluorophenyl)(hydroxy)methyl)-1-methyl-3-(3-(tetra hydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (55 mg, 0.10 mmol) in HCOOH (3 mL) was added Zn dust (40.4 mg, 0.62 mmol). The reaction was heated at 60° C. for 2 h then cooled to RT and filtered. The filtrate was concentrated to give 3-((6-(4-chlorophenoxy)-5-(4-fluorobenzyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propylformate (50 mg, 100% yield) as a white solid. LCMS: MH+ 498 and TR=1.732 min. Used without further purification.

Workup

temperaturethen cooled to RT
filtrationfiltered
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-d4a29e03d6af41408432c1030f884270
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440972B2

Reaction notes

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