Triethylamine → HCID 21876505, compound

HRID 724122Notes

Reaction equation

HRID 724122 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([CH3:12])[N:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=1.C(N(CC)CC)C>C1COCC1>[Cl:11][C:6]1[N:5]=[C:4]([CH3:12])[N:3]=[C:2]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=2)[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 669044-Aminophenethyl alcoholHCID 831924,6-Dichloro-2-methyl-5-nitropyrimidine

Product 1

HCID 21876505HCID 21876505, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4,6-dichloro-2-methyl-5-nitro-pyrimidine (Albert et al., J. Chem. Soc., 1954, 3832, 7.5 g, 36.1 mmol) in THF (150 ml) was added 4-aminophenylethyl alcohol (2.47 g, 18.0 mmol), triethylamine (3.65 g, 36.1 mmol), and the mixture was stirred at room temperature for 1 h. The reaction was quenched with water (10 ml), and the mixture was extracted with ethyl acetate (100 ml×3). The organic layer was washed with brine (50 ml), dried (MgSO4), and concentrated. Purification by flash column chromatography eluting with hexane/ethyl acetate (gradient elution from 1:1 to 1:2) to afford 4.0 g (72%) of the title compound as a yellow solid.

Workup

  1. customThe reaction was quenched with water (10 ml)
  2. extractionthe mixture was extracted with ethyl acetate (100 ml×3)
  3. washThe organic layer was washed with brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification by flash column chromatography
  7. washeluting with hexane/ethyl acetate (gradient elution from 1:1 to 1:2)

Sources & evidence

ORD record
ord-b6a7e613ed3840d6a358be58848a4b0e
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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