4,6-Dichloro-2-methylpyrimidine → 4-(6-Chloro-2-methyl-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester

HRID 448578Notes

Reaction equation

HRID 448578 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.C(O[K])(C)(C)C.[CH:16]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]1)=[O:21])([CH3:18])[CH3:17]>C1COCC1>[CH:16]([O:19][C:20]([N:22]1[CH2:23][CH2:24][CH:25]([O:28][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=2)[CH2:26][CH2:27]1)=[O:21])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 2349974,6-Dichloro-2-methylpyrimidineHCID 16745126Isopropyl 4-Hydroxypiperidine-1-carboxylateHCID 178418922HCID 178418922, compound

Product 1

HCID 866501764-(6-Chloro-2-methyl-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl esterYield 31.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4,6-Dichloro-2-methyl-pyrimidine (163 mg, 1 mmol) was dissolved in 4 mL of THF. A solution of tBuOK (112 mg, 1 mmol) and 2a (187 mg, 1 mmol) in 2 mL of THF was added slowly at room temperature. The mixture was stirred at room temperature for 8 h and quenched with a saturated solution of NH4Cl. The mixture was diluted with water and extracted with DCM. The organic layer was isolated, dried, filtered and evaporated to give 100 mg of 14a.

Workup

  1. customquenched with a saturated solution of NH4Cl
  2. additionThe mixture was diluted with water
  3. extractionextracted with DCM
  4. customThe organic layer was isolated
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-99a35504ce3642399d0d2b855b07ef43
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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