4,6-Dichloro-5-methylpyrimidine → 4-(6-Chloro-5-methyl-pyrimidin-4-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2377953Notes

Reaction equation

HRID 2377953 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([SH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[C:21]([CH3:22])=[C:20](Cl)[N:19]=[CH:18][N:17]=1.CC(C)([O-])C.[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:20]2[C:21]([CH3:22])=[C:16]([Cl:15])[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8188604,6-Dichloro-5-methylpyrimidineHCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 865973684-(6-Chloro-5-methyl-pyrimidin-4-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-mercapto-piperidine-1-carboxylic acid tert-butyl ester (1.5352 g, 7.06 mmol) and 4,6-dichloro-5-methyl-pyrimidine (1.1512 g, 7.06 mmol) in 15 mL of THF with sodium t-butoxide (1M in THF, 8.3 mL, 8.3 mmol) added dropwise. After 5 min, mixture was concentrated and residue was extracted with CH2Cl2 and H2O. Organic phase was dried over MgSO4, filtered and concentrated to give 4-(6-chloro-5-methyl-pyrimidin-4-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester as a yellowish solid (2.3469 g, 97%). Exact mass calculated for C15H22ClN3O2S 343.11, found 344.1 (MH+).

Workup

  1. additionadded dropwise
  2. concentrationmixture was concentrated
  3. extractionresidue was extracted with CH2Cl2 and H2O
  4. dry with materialOrganic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a48cf8283e44472c9471adeb7fd0d1f4
Source dataset
uspto-grants-2008_12
Patent number
US07470699B2

Reaction notes

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