Ethanol → 2-Isopropylamino-6-methyl-pyrimidine-4-carboxylic acid ethyl ester

HRID 2069420Notes

Reaction equation

HRID 2069420 reaction equation
[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[C:7]([CH3:14])[N:6]=1)([CH3:3])[CH3:2].[CH2:15](O)[CH3:16]>OS(O)(=O)=O>[CH2:15]([O:12][C:11]([C:9]1[CH:8]=[C:7]([CH3:14])[N:6]=[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])[N:10]=1)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 702EthanolHCID 669337152-(Isopropylamino)-6-methylpyrimidine-4-carboxylic acid

Product 1

HCID 685068162-Isopropylamino-6-methyl-pyrimidine-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid (1.27 g, 6.53 mmol) in ethanol (20 mL), concentrated H2SO4 (4 mL) is added. The reaction mixture is stirred at 80° C. for 18 h and is then evaporated. The residue is dissolved in EtOAc, washed with sat. aq. NaHCO3 and water, dried over MgSO4, filtered and evaporated. The crude compound is purified by CC on silica gel (eluting with Heptane/EtOAc 4:1) to give 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid ethyl ester as a yellow oil (1.46 g); LC-MS: tR=0.97; [M+H]+=224.49.

Workup

  1. customis then evaporated
  2. dissolutionThe residue is dissolved in EtOAc
  3. washwashed with sat. aq. NaHCO3 and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude compound is purified by CC on silica gel (eluting with Heptane/EtOAc 4:1)

Sources & evidence

ORD record
ord-6c7da20e7f7d407bbe59875753ee6b89
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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