1-Chloro-2,4-Dinitrobenzene → 3-(2-tert-Butoxyethoxy)-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 1660903Notes

Reaction equation

HRID 1660903 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]2[C:18](=[O:20])[NH:17][CH:16]=[N:15][C:14]=2[N:13]([CH3:21])[C:12](=[O:22])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].ClC1C=CC([N+]([O-])=O)=CC=1[N+]([O-])=O.[C:42]([O:46][CH2:47][CH2:48][O:49]N)([CH3:45])([CH3:44])[CH3:43]>CC(N(C)C)=O>[C:42]([O:46][CH2:47][CH2:48][O:49][N:17]1[C:18](=[O:20])[C:19]2[C:10]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=3[F:1])=[CH:11][C:12](=[O:22])[N:13]([CH3:21])[C:14]=2[N:15]=[CH:16]1)([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 11430Potassium CarbonateHCID 46856370O-(2-tert-butoxyethyl)hydroxylamineHCID 1357417325-((2-Fluoro-4-iodophenyl)amino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Product 1

HCID 581919373-(2-tert-Butoxyethoxy)-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneYield 12%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

Compound 5F (250 mg, 0.61 mmol), potassium carbonate (209 mg, 1.51 mmol) and 1-chloro-2,4-dinitrobenzene (307 mg, 1.51 mmol) were stirred in DMA at 80° C. for 1.5 h. O-(2-tert-Butoxy-ethyl)-hydroxylamine was added at r.t and the reaction was stirred for 1 h at 80° C. Purification by prep-HPLC gave 43 mg (12%) of the title compound as an off-white solid. MS (ES) [m+H] calc'd for C20H22FIN4O4, 529; found 529.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-5bfb155e7916496bb1cc787e050a9e44
Source dataset
uspto-grants-2011_10
Patent number
US08030317B2

Reaction notes

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