Diisopropylethylamine → HCID 71741777, compound

HRID 1843118Notes

Reaction equation

HRID 1843118 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[O:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:27][CH:24]2[CH2:25][CH2:26][O:21][CH2:22][CH2:23]2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 71741777HCID 71741777, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-64 °C

Procedure

To a solution of 2,4-dichloro-5-nitropyrimidine (1.03 g, 5.15 mmol) in THF (40 mL) at −78° C., DIPEA (2.0 mL, 11.86 mmol) and tetrahydro-2H-pyran-4-amine (0.54 mL, 5.15 mmol) were added. The reaction mixture was stirred from −78 to −50° C. for 5 h. The crude mixture was quenched with H2O (50 mL), extracted with EtOAc (3×40 mL) and the combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated. The crude product thus obtained was chromatographed over silica gel using EtOAc/hexanes mixtures of increasing polarity as eluent, to afford 1.04 g of the desired compound (78% yield).

Workup

  1. customThe crude mixture was quenched with H2O (50 mL)
  2. extractionextracted with EtOAc (3×40 mL)
  3. dry with materialthe combined organic phases were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product thus obtained
  7. customwas chromatographed over silica gel
  8. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-1f0defe958f34f23a1bfe74a0d4311d4
Source dataset
uspto-grants-2015_02
Patent number
US08946257B2

Reaction notes

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