Water → HCID 10491237, compound

HRID 599331Notes

Reaction equation

HRID 599331 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].O.Cl[C:7]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]([S:18][CH3:19])[N:8]=1>CC#N>[CH:1]([NH:4][C:11]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][N:8]=[C:9]([S:18][CH3:19])[N:10]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6363IsopropylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 10491237HCID 10491237, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of isopropylamine in water (7.6 g, 0.13 mol) was added dropwise to a solution of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (15 g, 64.7 mmol) in CH3CN (100 mL) at 0° C. The resulting mixture was stirred at RT for 8 h. The reaction was concentrated under reduced pressure and the residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (3×50 mL) and the combined organics were washed with brine, dried (MgSO4) and concentrated to give ethyl 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylate (16.4 g, 99% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.51 (s, 1 H), 8.05 (d, J=7.6 Hz, 1 H), 4.31-4.22 (m, 3 H), 2.46 (s, 3 H), 1.27 (t, J=7.2 Hz, 3H), 1.20 (d, J=6.4 Hz, 6 H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was partitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  4. washthe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9fcd76458e34443a86574f4bfc5228fa
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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