Hydrochloric Acid → 6-Cyclopropyl-2-hexylsulfanyl-pyrimidine-4-carbaldehyde

HRID 898128Notes

Reaction equation

HRID 898128 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([CH:10](OCC)[O:11]CC)[N:7]=[C:6]([S:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[N:5]=2)[CH2:3][CH2:2]1.Cl.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH:1]1([C:4]2[N:5]=[C:6]([S:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[N:7]=[C:8]([CH:10]=[O:11])[CH:9]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 692920874-Cyclopropyl-6-diethoxymethyl-2-hexylsulfanyl-pyrimidine

Product 1

HCID 860673446-Cyclopropyl-2-hexylsulfanyl-pyrimidine-4-carbaldehydeYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Cyclopropyl-6-diethoxymethyl-2-hexylsulfanyl-pyrimidine (2.7 g, 8 mmol) was dissolved in THF (13 mL) and 4 N HCl (13 mL) and stirred at 20° C. for 19 h. The reaction mixture was poured in cold 10% Na2CO3 (100 mL) and extracted twice with AcOEt and once with sat. NaCl solution. The crude product was purified by chromatography on silica gel in heptane/DCM with a gradient of 100:0 to 67:33. One obtained 2 g (94%) of a yellow oil, which solidified upon standing in the fridge. MS: m/z=264 (M).

Workup

  1. extractionextracted twice with AcOEt and once with sat. NaCl solution
  2. customThe crude product was purified by chromatography on silica gel in heptane/DCM with a gradient of 100:0 to 67:33

Sources & evidence

ORD record
ord-1d36302599644768aea66d31e4df5439
Source dataset
uspto-grants-2008_04
Patent number
US07351700B2

Reaction notes

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