Morpholine → HCID 59198390, compound

HRID 1920824Notes

Reaction equation

HRID 1920824 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:13][CH:14]=2)[N:3]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(CC)CC)C>CN1C(=O)CCC1>[Cl:8][C:6]1[CH:7]=[C:2]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[N:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:13][CH:14]=2)[N:5]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 59198375HCID 59198375, compound

Product 1

HCID 59198390HCID 59198390, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-(5-(4,6-dichloropyrimidin-2-yl)pyridine-2-yl)pivalamide (975 mg, 3.0 mmol), morpholine (0.262 mL, 3.0 mmol) and triethylamine (502 mL, 3.6 mmol) are stirred in NMP (10 mL) for 2 hours at 85° C. At this time the reaction mixture is partitioned between EtOAc (200 mL) and NaHCO3(sat.) (50 mL). The organic layer is separated, washed with water (30 mL), then brine (30 mL), dried over Na2SO4, filtered, concentrated, obtaining the desired product.

Workup

  1. customAt this time the reaction mixture is partitioned between EtOAc (200 mL) and NaHCO3(sat.) (50 mL)
  2. customThe organic layer is separated
  3. washwashed with water (30 mL)
  4. dry with materialbrine (30 mL), dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-320d58bf8c93472b9970be09ca113be2
Source dataset
uspto-grants-2012_05
Patent number
US08173647B2

Reaction notes

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