Dimethylamine → HCID 117819038, compound

HRID 1753221Notes

Reaction equation

HRID 1753221 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:13].[CH3:14][NH:15][CH3:16].C1COCC1.C(N(C(C)C)CC)(C)C>O1CCOCC1.O>[CH3:14][N:15]([CH3:16])[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:13]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 56592992Ethyl 6-chloro-5-methylpyrimidine-4-carboxylate

Product 1

HCID 117819038HCID 117819038, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 6-chloro-5-methylpyrimidine-4-carboxylate (41) (80 g, 398.0 mmol) dissolved in dioxane (800 ml) were added dimethyl amine in THF (2M, 600 ml, 1196.0 mmol) and diisopropyl ethylamine (330 ml, 1990.0 mmol). The reaction mixture was heated to 80° C. for 16 h. Then the mixture is cooled to room temperature, diluted with water, and extracted with EtOAc (2×50 mL). The combined organic layer was washed with water, brine, dried over sodium sulfate, and concentrated at reduced pressure to yield ethyl 6-(dimethylamino)-5-methylpyrimidine-4-carboxylate (45) as a light yellow liquid; yield: 60 g (72%).

Workup

  1. temperatureThen the mixture is cooled to room temperature
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-4a4ee7d2e44b4c1189fd8f34a526b0ef
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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