Methanesulfonic Acid → 5-(Diisopropoxymethyl)-2-methylpyrimidine

HRID 512199

Reaction equation

HRID 512199 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5](C=O)=[CH:4][N:3]=1.C(O[CH:14]([O:19][CH:20]([CH3:22])[CH3:21])[O:15][CH:16]([CH3:18])[CH3:17])(C)C.CS(O)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH:20]([O:19][CH:14]([O:15][CH:16]([CH3:17])[CH3:18])[C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[N:7][CH:6]=1)([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 11430Potassium CarbonateHCID 78191Propane, 2,2',2''-[methylidynetris(oxy)]tris-HCID 31609702-Methylpyrimidine-5-carbaldehyde

Product 1

HCID 867162275-(Diisopropoxymethyl)-2-methylpyrimidineYield 29.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2-methylpyrimidine-5-carbaldehyde (1.0 g, 8.2 mmol) and triisopropoxymethane (2.3 g, 12 mmol) in isopropanol (15 ml) was added methanesulfonic acid (0.079 g, 0.053 ml, 0.819 mmol). The reaction was stirred at room temperature for 23 hours. Potassium carbonate (1.132 g, 8.19 mmol) was added and the mixture was filtered and the solution was concentrated in vacuo. The crude mixture was purified by flash chromatography to yield 5-(diisopropoxymethyl)-2-methylpyrimidine (536 mg, 29%)

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe solution was concentrated in vacuo
  3. customThe crude mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-4fe02f5b96f2459190c5311e99599d9b
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Linked notes

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