Morpholine → HCID 178493075, compound

HRID 415445Notes

Reaction equation

HRID 415445 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:19]=[C:18]([O:20][CH3:21])[NH:17][N:16]=2)[C:11]([F:22])=[C:10](Cl)[N:9]=1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:7][C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:19]=[C:18]([O:20][CH3:21])[NH:17][N:16]=2)[C:11]([F:22])=[C:10]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:9]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 178493074HCID 178493074, compound

Product 1

HCID 178493075HCID 178493075, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,4,6-trichloro-5-fluoropyrimidine (2.01 g) in absolute ethanol (50 mL) was added DIEPA (4.4 mL) and 5-methoxy-1H-pyrazol-3-amine (2.24 g). The resulting solution was stirred at room temperature for over night. The solvent was removed by reduced pressure and the residue was purified by Gilson (10-50% MeCN/H2O, 15 minutes) to give the titled compound 2,6-dichloro-5-fluoro-N-(5-methoxy-1H-pyrazol-3-yl)pyrimidin-4-amine as solid (0.776 g). m/z 278. A mixture of morpholine (0.256 mL), 2,6-dichloro-5-fluoro-N-(5-methoxy-1H-pyrazol-3-yl)pyrimidin-4-amine (776 mg) and DIPEA (0.742 ml) in n-butanol (14.0 ml) was heated at 90° C. for 5 hours. The solvent was removed under reduced pressure and the residue was purified by Gilson (10-50% MeCN/H2O, 15 minutes) to give the titled compound as solid (310 mg). 1H NMR 9.80 (s, 1H) 5.66 (s, 1H) 3.77 (s, 3H) 3.64-3.71 (m, 4H) 3.53-3.64 (m, 4H); m/z 329.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by Gilson (10-50% MeCN/H2O, 15 minutes)

Sources & evidence

ORD record
ord-d4160d542e2e4359b962d351b09f3afb
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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