HCID 118875490, compound → 3-(6-bromo-1-methyl-2,4-dioxo-5((6-(trifluoromethyl)pyridin-3-yl)methyl)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propylformate

HRID 60505Notes

Reaction equation

HRID 60505 reaction equation
[Br:1][C:2]1[CH:24]=[N:23][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH:15]3CCCC[O:16]3)[C:9](=[O:10])[C:4]=2[C:3]=1[CH:25](O)[C:26]1[CH:27]=[N:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=1>C(O)=O.[Zn]>[Br:1][C:2]1[CH:24]=[N:23][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH:15]=[O:16])[C:9](=[O:10])[C:4]=2[C:3]=1[CH2:25][C:26]1[CH:27]=[N:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 118875490HCID 118875490, compound

Product 1

HCID 1188758833-(6-bromo-1-methyl-2,4-dioxo-5((6-(trifluoromethyl)pyridin-3-yl)methyl)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propylformateYield 57.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 6-bromo-5-(hydroxy(6-(trifluoromethyl)pyridin-3-yl)methyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (160 mg, 0.280 mmol) in formic acid (2 mL) was added Zinc dust (40.9 mg, 0.64 mmol). The reaction was heated at 50° C. for 2 h, cooled to RT and filtered. The filtrate was concentrated to a residue which was purified by chromatography eluted with PE/EA (10:1) to give 3-(6-bromo-1-methyl-2,4-dioxo-5((6-(trifluoromethyl)pyridin-3-yl)methyl)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propylformate (80 mg, 57.1% yield). LCMS: MH+ 501 and TR=1.727 min.

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to a residue which
  4. customwas purified by chromatography
  5. washeluted with PE/EA (10:1)

Sources & evidence

ORD record
ord-2e04ce5c9d4f42e099dd8dbd4ab52e49
Source dataset
uspto-grants-2016_09
Patent number
US09440972B2

Reaction notes

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