Isopropylamine → HCID 10491237, compound

HRID 1783553Notes

Reaction equation

HRID 1783553 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.C(N(CC)CC)C.[CH:22]([NH2:25])([CH3:24])[CH3:23]>ClCCl.C(OCC)(=O)C>[CH:22]([NH:25][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1)([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 10491237HCID 10491237, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 10.0 g (43.0 mmol) of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate and 7.2 mL (51.6 mmol) of triethylamine in 100 mL of dichloromethane is added 4.4 mL (51.6 mmol) of isopropylamine. The reaction solution is stirred at 0° C. for 2 hours then allowed to warm to room temperature. The reaction mixture is diluted with ethyl acetate, washed twice with aqueous HCl, twice with water, once with a saturated solution of sodium bicarbonate, and brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated to give 11.1 g (quant.) of the title compound as an oil which solidified on standing: mp 159-160° C.

Workup

  1. temperatureto warm to room temperature
  2. washwashed twice with aqueous HCl, twice with water, once with a saturated solution of sodium bicarbonate, and brine
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8873e0a4b3a2442eba1a48d62786bdc7
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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