Triethylamine → HCID 67021320, compound

HRID 1868453Notes

Reaction equation

HRID 1868453 reaction equation
N[CH2:2][C:3]1[C:4]([CH3:24])=[N:5][C:6]2[N:7]([N:17]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16].[O:25](C(OC(C)(C)C)=O)[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=O.CCN(CC)CC>C1COCC1>[C:29]([O:28][C:26]([CH2:2][C:3]1[C:4]([CH3:24])=[N:5][C:6]2[N:7]([N:17]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[N:19]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])=[O:25])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 11537890HCID 11537890, compound

Product 1

HCID 67021320HCID 67021320, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 6-(aminomethyl)-7-(2,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate (Example 27, 50 mg, 0.14 mmol) in THF (3 mL) was added (BOC)2O (75 μL, 0.34 mmol) and Et3N (100 μl, 0.70 mmol). After 2 h, the reaction was concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with satd aq NH4Cl and brine prior to drying over anhydrous MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography (50% EtOAc in hexanes) afforded methyl 6-((tert-butoxycarbonyl)methyl)-7-(2,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate (13 mg, 20%) as a white solid.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with satd aq NH4Cl and brine
  4. dry with materialto drying over anhydrous MgSO4
  5. filtrationFiltration, concentration
  6. customunder reduced pressure and purification by silica gel chromatography (50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ed14958075434cd59b15f0a3e0c52d4c
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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