Cesium carbonate → HCID 59605221, compound

HRID 1945629Notes

Reaction equation

HRID 1945629 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:12]=[O:13])[N:8]2[CH3:11])=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1.[CH:20]1([C:23]2[NH:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)[CH2:22][CH2:21]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CN(C=O)C.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:20]1([C:23]2[N:24]([C:2]3[N:10]=[C:9]4[C:5]([N:6]=[C:7]([CH:12]=[O:13])[N:8]4[CH3:11])=[C:4]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[N:3]=3)[C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)[CH2:22][CH2:21]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 10844192-cyclopropyl-1H-1,3-benzodiazoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 596034722-Chloro-9-methyl-6-morpholino-9H-purine-8-carbaldehyde

Product 1

HCID 59605221HCID 59605221, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 2-chloro-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (210 mg, 0.79 mmol), 2-cyclopropylbenzimidazole (150 mg, 0.95 mmol), tris(dibenzylideneacetone)dipalladium (44 mg, 0.05 mmol), Xphos (90 mg, 0.18 mmol) and Cs2CO3 (618 mg, 1.90 mmol) in dioxane (3 mL) and DMF (1 mL) was purged with argon then heated at 145° C. for 45 min in a microwave reactor. The reaction mixture was filtered through a pad of celite, washing with EtOAc. The filtrate was concentrated in vacuo and purified by column chromatography (Si—PCC, EtOAc:cyclohexane, 0-75%) affording 2-(2-Cyclopropylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde as an orange solid (282 mg, 89%). LCMS (Method H): RT 3.79 min, [M+H]+ 436.4

Workup

  1. customwas purged with argon
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washwashing with EtOAc
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by column chromatography (Si—PCC, EtOAc:cyclohexane, 0-75%)

Sources & evidence

ORD record
ord-daefae75ae8c478fbeede2d8f1bcff50
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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