Morpholine → 7-Morpholinopyrazolo[1,5-a]pyrimidin-5-amine

HRID 1409131Notes

Reaction equation

HRID 1409131 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 582073347-Morpholinopyrazolo[1,5-a]pyrimidin-5-amineYield 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-fb968def7fdb4e228bd93243036a54d3
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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