Morpholine → HCID 58207334, compound

HRID 1256290Notes

Reaction equation

HRID 1256290 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([NH2:11])[CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CN1C(=O)CCC1>O1CCOCC1>[O:15]1[CH2:16][CH2:17][N:12]([C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[C:4]([NH2:11])[CH:3]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 13387N-methyl-2-pyrrolidoneHCID 442513067-Chloropyrazolo[1,5-a]pyrimidin-5-amine

Product 1

HCID 58207334HCID 58207334, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

7-Chloropyrazolo[1,5-a]pyrimidin-5-amine (1E, 10 g, 30 mmol) and morpholine were added to NMP (20 ml) and dioxane (80 ml). The mixture was heated to 100° C. and the resulting suspension was concentrated in vacuo to remove most of the dioxane. Brine was added and the mixture was extracted with EtOAc five times. Combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Trituration of the residue with Et2O gave the desired product 7-morpholinopyrazolo[1,5-a]pyrimidin-5-amine (9A, 5.0 g, 38%) as an off-white solid.

Workup

  1. concentrationthe resulting suspension was concentrated in vacuo
  2. customto remove most of the dioxane
  3. additionBrine was added
  4. extractionthe mixture was extracted with EtOAc five times
  5. washCombined organics were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a9ee45bdec94c6c92b322f155cf28dc
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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