Diethyl Ether → HCID 59823039, compound

HRID 1260438Notes

Reaction equation

HRID 1260438 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15](Cl)=[C:16]([CH3:21])[C:17](=[O:20])[N:18]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:25]=1[NH2:26].CC(C)([O-])C.[Na+].C(OCC)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([NH:26][C:25]3[CH:27]=[CH:28][C:29]([N+:31]([O-:33])=[O:32])=[CH:30][C:24]=3[F:23])=[C:16]([CH3:21])[C:17](=[O:20])[N:18]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 1012542-Fluoro-4-nitroanilineHCID 23676156Sodium t-butoxideHCID 59823064HCID 59823064, compound

Product 1

HCID 59823039HCID 59823039, compoundYield 42.4%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-Benzyl-5-chloro-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (7 g, 22.2 mmol, 1 eq), 2-fluoro-4-nitroaniline (53.8 mg, 24.4 mmol, 1.1 eq), tris(dibenzylideneacetone)dipalladium(0) (407 mg, 0.44 mmol, 0.02 eq), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (257 mg, 0.44 mmol, 0.02 eq) and sodium tert-butoxide (3.2 g, 0.33 mmol, 1.5 eq) were mixed in degassed anhydrous dioxane (50 mL) and subjected to microwave irradiation at 115° C. for 40 minutes. Upon cooling diethyl ether (50 mL) was added. A precipitate formed which was filtered and washed with ether to give 4.1 g of the title compound (42%). [M+H] calc'd for C22H18FN5O4, 436. found, 436.

Workup

  1. customirradiation at 115° C. for 40 minutes
  2. additionwas added
  3. customA precipitate formed which
  4. filtrationwas filtered
  5. washwashed with ether

Sources & evidence

ORD record
ord-ba8c4fdc9e6c40e3b56193787ac50de3
Source dataset
uspto-grants-2013_06
Patent number
US08470837B2

Reaction notes

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