Water → HCID 58382518, compound

HRID 1027475Notes

Reaction equation

HRID 1027475 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]([O:20][CH2:21][CH2:22][CH3:23])[C:6]2[N:11]=[C:10]([C:12]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=3[Cl:19])[O:9][C:7]=2[N:8]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.ClCCl>[Cl:19][C:13]1[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=1[C:10]1[O:9][C:7]2[N:8]=[C:3]([CH2:2][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:4]=[C:5]([O:20][CH2:21][CH2:22][CH3:23])[C:6]=2[N:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 67176227HCID 67176227, compound

Product 1

HCID 58382518HCID 58382518, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 130 mg of 5-bromomethyl-2-(2-chloro-5-fluoro-phenyl)-7-propoxy-oxazolo[5,4-d]pyrimidine, 33.9 mg of morpholine and 135 mg of potassium carbonate in 3 ml of dimethylformamide was stirred at room temperature for 4 h. Then 50 ml water and 50 ml of dichloromethane were added. The phases were separated and the aqueous layer was extracted with 50 ml of dichloromethane. The combined organic layers were dried with sodium sulfate, filtered, and evaporated in vacuo. The residue was purified by preparative HPLC (Method HPLC1) to give 72 mg of the title compound in the form of 2-(2-chloro-5-fluoro-phenyl)-5-morpholin-4-ylmethyl-7-propoxy-oxazolo[5,4-d]pyrimidine trifluoroacetic acid salt.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with 50 ml of dichloromethane
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative HPLC (Method HPLC1)

Sources & evidence

ORD record
ord-be9c6f8dc44842f8abb84c4213535429
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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