Ammonia → HCID 118433871, compound

HRID 1052451Notes

Reaction equation

HRID 1052451 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH3:21].Cl>O1CCOCC1>[NH2:21][C:6]1[C:7]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:9])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 90102454HCID 90102454, compound

Product 1

HCID 118433871HCID 118433871, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

4,6-Dichloro-N-(3-morpholinopropyl)pyrimidine-5-carboxamide (1.13 g, 3.08 mmol) was dissolved in dioxane (10 ml) and cooled in an ice bath. Ammonia solution (2.2 ml, 7N in MeOH) was added dropwise and the mixture was stirred at 0° C. for 15 min and 4 h at room temperature. After dilution with ethyl acetate, this organic phase was washed with water and brine, dried over magnesium sulphate, filtered and the solvents evaporated under reduced pressure, to yield an oil which was rejected. The aqueous phase was neutralized with 2N HCl, extracted with DCM, dried over magnesium sulphate, filtered and the solvent evaporated. An oil was obtained (450 mg, 70% purity, 34% yield) which was used in the next synthetic step without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. washAfter dilution with ethyl acetate, this organic phase was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvents evaporated under reduced pressure
  6. customto yield an oil which
  7. extractionextracted with DCM
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customthe solvent evaporated
  11. customAn oil was obtained (450 mg, 70% purity, 34% yield) which
  12. customwas used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-a7de80c8266a486299496618104fe0a6
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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