Water → Methyl 2-chloro-6-(cyclohexylamino)pyrimidine-4-carboxylate

HRID 1746642Notes

Reaction equation

HRID 1746642 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[N:3]=1.[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C.O>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=[C:6]([NH:19][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7965CyclohexylamineHCID 8471TriethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylate

Product 1

HCID 59447049Methyl 2-chloro-6-(cyclohexylamino)pyrimidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled (0° C.) solution of methyl 2,4-dichloropyrimidine-6-carboxylate (Apollo, OR2558, 10.00 g; 48.31 mmol) in THF (300 mL) was treated with a solution of cyclohexylamine (Fluka, 5.53 mL; 48.3 mmol) and triethylamine (7.37 mL; 53.1 mmol) in THF (100 mL). The reaction mixture was stirred for 16 hours at RT. Water (50 mL) was poured into the reaction mixture which was extracted with EtOAc. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to obtain the crude product, which was purified by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc. The title product was obtained as a white solid.

Workup

  1. extractionwas extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto obtain the crude product, which
  6. customwas purified by column chromatography (silica)
  7. washeluting with cyclohexane containing
  8. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-f91384dd2434401e9394a48bdbe113c1
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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