1,2-Dimethoxyethane → HCID 53492458, compound

HRID 1851637Notes

Reaction equation

HRID 1851637 reaction equation
[NH2:1][C:2]1[N:3]([CH3:24])[C:4](=[O:23])[C:5]2([N:22]=1)[C:18]1[CH:17]=[C:16](Br)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([O:20][CH3:21])=[CH:9][CH:10]=1.[N:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[N:27][CH:26]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>CCOC(C)=O.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]([CH3:24])[C:4](=[O:23])[C:5]2([N:22]=1)[C:6]1[CH:7]=[C:8]([O:20][CH3:21])[CH:9]=[CH:10][C:11]=1[O:12][C:13]1[C:18]2=[CH:17][C:16]([C:29]2[CH:30]=[N:25][CH:26]=[N:27][CH:28]=2)=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 67457946HCID 67457946, compound

Product 1

HCID 53492458HCID 53492458, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A 15 ml resealable vial was charged with 2-amino-2′-bromo-7′-methoxy-1-methylspiro[imidazole-4,9′-xanthen]-5(1H)-one (87 mg, 224 μmol), pyrimidin-5-ylboronic acid (56 mg, 448 μmol) and tetrakis(triphenylphosphine)palladium(0) (26 mg, 22 μmol). DME (1 ml) was added to the mixture, and the vial was capped with argon. Sodium carbonate (2M aq. solution) (336 μl, 672 μmol) was added and the vial was sealed and heated at 85° C. for 16 hr. The heterogeneous mixture was cooled to RT, diluted with 5 ml EtOAc and 2 ml water, then filtered and the solids were washed with water (5 ml). The solids were redissolved in DCM/MeOH and dried with MgSO4, filtered and concentrated in vacuo to afford 2-amino-2′-methoxy-1-methyl-7′-(pyrimidin-5-yl)spiro[imidazole-4,9′-xanthen]-5(1H)-one as brownish solid.

Workup

  1. customthe vial was capped with argon
  2. customthe vial was sealed
  3. temperatureThe heterogeneous mixture was cooled to RT
  4. filtrationfiltered
  5. washthe solids were washed with water (5 ml)
  6. dissolutionThe solids were redissolved in DCM/MeOH
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04bb283621264de48ab459bb7b3410d1
Source dataset
uspto-grants-2015_02
Patent number
US08957083B2

Reaction notes

Loading…