Water → HCID 58382520, compound

HRID 1027498Notes

Reaction equation

HRID 1027498 reaction equation
O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[Cl:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][C:23]2[N:24]=[C:25]([O:34][CH2:35][CH2:36][CH3:37])[C:26]3[N:31]=[C:30](SC)[O:29][C:27]=3[N:28]=2)=[CH:20][CH:19]=1.[NH2:40][C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][CH:46]=1.O>O1CCCC1.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].S1C=CC=C1C([O-])=O.[Cu+].C(OCC)(=O)C>[Cl:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][C:23]2[N:24]=[C:25]([O:34][CH2:35][CH2:36][CH3:37])[C:26]3[N:31]=[C:30]([C:45]4[CH:46]=[C:41]([NH2:40])[CH:42]=[CH:43][CH:44]=4)[O:29][C:27]=3[N:28]=2)=[CH:20][CH:19]=1

Participants

9

Reactant 4

HCID 962WaterHCID 922693-Aminophenylboronic acidHCID 521585Tris(furan-2-yl)phosphaneHCID 67176736HCID 67176736, compound

Product 1

HCID 58382520HCID 58382520, compoundYield 31.2%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 11194830Cuprous 2-thiophenecarboxylateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Under argon atmosphere, 13.1 mg of tris(dibenzylideneacetone)dipalladium and 13.3 mg of tri(furan-2-yl)phosphine were added to a solution of 125 mg of 5-(4-chloro-benzyl)-2-methylsulfanyl-7-propoxy-oxazolo[5,4-d]pyrimidine, 81.7 mg of copper(I)thiophene-2-carboxylate and 58.7 mg of 3-amino-benzeneboronic acid in 3.5 ml of tetrahydrofuran. The mixture was heated to 80° C. for 2 h in a microwave reactor (CEM Discover). After cooling, 3 ml of water and 3 ml of ethyl acetate were added. The mixture was filtered through a ChemElut cartridge and the cartridge washed with ethyl acetate. The combined filtrates were evaporated in vacuo. Preparative HPLC (method HPLC1) of the residue yielded 44 mg of the title compound in the form of the 3-[5-(4-chloro-benzyl)-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl]-phenylamine trifluoroacetic acid salt.

Workup

  1. temperatureAfter cooling
  2. filtrationThe mixture was filtered through a ChemElut cartridge
  3. washthe cartridge washed with ethyl acetate
  4. customThe combined filtrates were evaporated in vacuo

Sources & evidence

ORD record
ord-68cfa3a0d69a42da8a4ec561f71d8c5d
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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