Potassium Carbonate → HCID 67129987, compound

HRID 1038853Notes

Reaction equation

HRID 1038853 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:11][CH:12]2[CH2:14][CH2:13]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH:21]([CH3:27])[C:22](=[O:26])[NH:23]2)=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)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]>[CH:12]1([NH:11][C:4]2[C:5]3[O:10][CH:9]=[CH:8][C:6]=3[N:7]=[C:2]([NH:15][C:16]3[CH:25]=[C:24]4[C:19]([CH2:20][CH:21]([CH3:27])[C:22](=[O:26])[NH:23]4)=[CH:18][CH:17]=3)[N:3]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 157190337-amino-3-methyl-3,4-dihydroquinolin-2(1H)-oneHCID 866650932-chloro-N-cyclopropylfuro[3,2-d]pyrimidin-4-amine

Product 1

HCID 67129987HCID 67129987, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with 2-chloro-N-cyclopropylfuro[3,2-d]pyrimidin-4-amine (0.38 g, 1.8 mmol, Example #3, Step C), 7-amino-3-methyl-3,4-dihydroquinolin-2(1H)-one (0.30 g, 1.7 mmol), K2CO3 (0.38 g, 2.7 mmol), Pd2dba3 (0.17 g, 0.18 mmol) and X-Phos (0.17 g, 0.36 mmol) in 1,4-dioxane (20 mL). The flask was evacuated and purged with N2 (3×), and the mixture was heated to about 100° C. overnight. The mixture was cooled to rt and concentrated under reduced pressure to a residue. The residue was purified by preparative TLC (1.0 mm plate), eluting with DCM/MeOH (12:1). The product obtained was further purified by preparative HPLC (Table 2, Method r) to give 7-(4-(cyclopropylamino)furo[3,2-d]pyrimidin-2-ylamino)-3-methyl-3,4-dihydroquinolin-2(1H)-one (0.15 g, 24%): LC/MS (Table 2, Method g) Rt=1.04 min; MS m/z: 177 (M+H)+. Syk IC50=A

Workup

  1. customThe flask was evacuated
  2. custompurged with N2 (3×)
  3. temperatureThe mixture was cooled to rt
  4. concentrationconcentrated under reduced pressure to a residue
  5. customThe residue was purified by preparative TLC (1.0 mm plate)
  6. washeluting with DCM/MeOH (12:1)
  7. customThe product obtained
  8. customwas further purified by preparative HPLC (Table 2, Method r)

Sources & evidence

ORD record
ord-93e5a8f7466f4f44a9ed2918ab0aaa13
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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