Cyanogen Bromide → HCID 86699282, compound

HRID 2278651Notes

Reaction equation

HRID 2278651 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[N:7]#[C:8]Br.[N:10]1([C:19](=[O:34])[CH2:20][C:21]2[NH:26][C:25](=[O:27])[CH:24]=[C:23]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[N:22]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1>O1CCOCC1>[N:10]1([C:19](=[O:34])[CH2:20][C:21]2[N:26]([C:8]#[N:7])[C:25](=[O:27])[CH:24]=[C:23]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[N:22]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 10796Cesium carbonateHCID 1360417572-[2-(2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one

Product 1

HCID 86699282HCID 86699282, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

330 mg of cesium carbonate and 404 mg of cyanogen bromide are successively added to a solution of 1 g 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 example 41d, step 1d) in 40 ml of dioxane with 4 Å molecular sieve. The reaction mixture is heated at 40° C. for 2 hours and then cooled to ambient temperature. The suspension is filtered through sintered glass and then rinsed with dioxane, and the filtrate is concentrated 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. The residue is taken up with a mixture of 3 ml of methanol and 10 ml of ethyl ether. After stirring and filtration, the precipitate obtained is rinsed with ethyl ether (3×2 ml) and 22 mg of 2-[2-(2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-4-(morpholin-4-yl)-6-oxopyrimidine-1(6H)-carbonitrile are obtained in the form of a beige solid, the characteristics of which are the following:

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe suspension is filtered through sintered glass
  3. washrinsed with dioxane
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is purified by silica column chromatography, elution
  6. additionbeing carried out with a mixture of dichloromethane and methanol (95/05)
  7. additionThe fractions of interest containing the product
  8. customevaporated under reduced pressure
  9. additionThe residue is taken up with a mixture of 3 ml of methanol and 10 ml of ethyl ether
  10. filtrationfiltration
  11. customthe precipitate obtained
  12. washis rinsed with ethyl ether (3×2 ml) and 22 mg of 2-[2-(2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-4-(morpholin-4-yl)-6-oxopyrimidine-1(6H)-carbonitrile
  13. customare obtained in the form of a beige solid

Sources & evidence

ORD record
ord-0aadcb7bf7ab4115a945f82d67ac5320
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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