Isopropyl chloroformate → HCID 86597369, compound

HRID 2377955Notes

Reaction equation

HRID 2377955 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([S:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.Cl[C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25]>CC#N>[CH:27]([O:26][C:24]([N:13]1[CH2:14][CH2:15][CH:10]([S:9][C:6]2[C:7]([CH3:8])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=2)[CH2:11][CH2:12]1)=[O:25])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 860222804-Chloro-5-methyl-6-(piperidin-4-ylsulfanyl)-pyrimidine

Product 1

HCID 86597369HCID 86597369, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-5-methyl-6-(piperidin-4-ylsulfanyl)-pyrimidine (HCl salt, 1.8985 g, 6.77 mmol) and triethylamine (2.825 mL, 0.02 mol) in 50 mL of CH3CN was stirred under room temperature. After 15 min, isopropyl chloroformate (1M in toluene, 8.13 mL, 8.13 mmol) were added slowly under 0° C. Mixture was stirred under room temperature. After 3 h, mixture was concentrated and residue was extracted with EtOAc and saturated NaHCO3. Organic phase was dried over MgSO4, filtered and concentrated to give 4-(6-chloro-5-methyl-pyrimidin-4-ylsulfanyl)-piperidine-1-carboxylic acid isopropyl ester as yellowish oil (1.9143 g, 85%). Exact mass calculated for C14H20ClN3O2S 329.1, found 330.3 (MH+).

Workup

  1. stirringMixture was stirred under room temperature
  2. waitAfter 3 h
  3. concentrationmixture was concentrated
  4. extractionresidue was extracted with EtOAc and saturated NaHCO3
  5. dry with materialOrganic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5c6d8d2ef31a433e88d36d810c1604db
Source dataset
uspto-grants-2008_12
Patent number
US07470699B2

Reaction notes

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