Potassium Carbonate → HCID 58019807, compound

HRID 1099113Notes

Reaction equation

HRID 1099113 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([O:13][CH2:14][CH3:15])[C:5]2[N:11]=[C:10](Cl)[CH:9]=[CH:8][C:6]=2[N:7]=1.[CH:16]1([NH:19][C:20]([C:22]2[S:23][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:25][CH:26]=2)=[O:21])[CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:3]=[C:4]([O:13][CH2:14][CH3:15])[C:5]2[N:11]=[C:10]([C:24]3[S:23][C:22]([C:20](=[O:21])[NH:19][CH:16]4[CH2:18][CH2:17]4)=[CH:26][CH:25]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 58019804HCID 58019804, compoundHCID 597672176-Chloro-4-ethoxypyrido[3,2-d]pyrimidin-2-amine

Product 1

HCID 58019807HCID 58019807, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-amino-4-ethoxy-6-chloropyrido[3,2-d]pyrimidine (50 mg) in 1,4-dioxane (7 ml) and water (2.5 ml) was added N-(cyclopropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarboxamide (72 mg), K2CO3 (77 mg) and tetrakis(triphenylphosphine)palladium(0) (13 mg). The reaction mixture was heated to 90° C. for 1 hour. The reaction mixture was extracted with dichloromethane after which the organic layer was concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography, the mobile phase being a 3:97 MeOH/CH2Cl2 mixture, resulting in the pure title compound as a white powder (64 mg, yield: 81%) which was characterized by its mass spectrum as follows: MS (m/z): 356 ([M+H]+, 100).

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane after which the organic layer
  2. concentrationwas concentrated under reduced pressure
  3. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c80a8fc2507747e5a5e18672a03da6ed
Source dataset
uspto-grants-2012_03
Patent number
US08143394B2

Reaction notes

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