Ethylamine → Ethyl 4-(ethylamino)-2-(methylthio)pyrimidine-5-carboxylate

HRID 1930395Notes

Reaction equation

HRID 1930395 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[CH2:15]([NH2:17])[CH3:16]>CC#N>[CH2:15]([NH:17][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1)[CH3:16]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 10514260Ethyl 4-(ethylamino)-2-(methylthio)pyrimidine-5-carboxylateYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 0° C. solution of ethyl 4-chloro-2(methylthio)pyrimidine-5-carboxylate (19 g, 82 mmol) in CH3CN (100 mL) was added a solution of aqueous ethylamine (70%, 8.1 g, 126 mmol). The resulting mixture was stirred at RT for 8 h. The organic solution was removed under reduced pressure, and the residue was partitioned between EtOAc and H2O. The aqueous layer was extracted with ethyl acetate (3×30 mL) and the combined organics were washed with brine, dried (MgSO4) and concentrated to give ethyl 4-(ethylamino)-2-(methylthio)pyrimidine-5-carboxylate (19.5 g, 99.1% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.49 (s, 1 H), 8.26 (t, J=4.8 Hz, 1 H), 4.23 (q, J=7.2 Hz, 2 H), 3.48 (q, J=7.2 Hz, 2 H), 2.44 (s, 3 H), 1.26 (t, J=7.2 Hz, 3 H), 1.13 (t, J=7.2 Hz, 3 H).

Workup

  1. customThe organic solution was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and H2O
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×30 mL)
  4. washthe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b8f767974a504906aaca7843eb8d90a1
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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