Dimethylformamide → HCID 68281588, compound

HRID 2278650Notes

Reaction equation

HRID 2278650 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[N:7]1([C:16](=[O:31])[CH2:17][C:18]2[NH:23][C:22](=[O:24])[CH:21]=[C:20]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:19]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1.C[N:33](C)C=O>O>[NH2:33][N:23]1[C:22](=[O:24])[CH:21]=[C:20]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[N:19]=[C:18]1[CH2:17][C:16]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1)=[O:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 1360417572-[2-(2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one

Product 1

HCID 68281588HCID 68281588, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

957 mg of cesium carbonate and 685 mg of o-diphenylphosphinylhydroxylamine are successively added to a suspension of 500 mg of 2-[2-(2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one (which can be obtained according to the previous step) in 5 ml of dimethylformamide. The reaction mixture is stirred at ambient temperature for 2 hours and then diluted with 10 ml of water and extracted with dichloromethane (3×25 ml). The organic phases are combined and then dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of dichloromethane and methanol (95/05). The fractions of interest containing the product are combined and then evaporated under reduced pressure, and 154 mg of 3-amino-2-[2-(2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a pale yellow solid, the characteristics of which are the following:

Workup

  1. customcan be obtained
  2. extractionextracted with dichloromethane (3×25 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue is purified by silica column chromatography, elution
  7. additionbeing carried out with a mixture of dichloromethane and methanol (95/05)
  8. additionThe fractions of interest containing the product
  9. customevaporated under reduced pressure, and 154 mg of 3-amino-2-[2-(2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one
  10. customare obtained in the form of a pale yellow solid

Sources & evidence

ORD record
ord-1e3809e08fbe40f7907335d4cd416f41
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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