Diethyl Ether → HCID 11240873, compound

HRID 1826586Notes

Reaction equation

HRID 1826586 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[CH3:12][Mg]Br.C(OCC)C>O1CCCC1>[NH2:1][C:2]1[C:7]([CH:8]([OH:9])[CH3:12])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehydeHCID 178418573HCID 178418573, compound2×

Product 1

HCID 11240873HCID 11240873, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5.0 g (29 mmol) 4-amino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde (Example 3) in 150 mL of tetrahydrofuran, cooled by an ice bath, is added during 20 minutes. 23.2 mL of a 3.0 M methylmagnesium bromide solution in diethyl ether (69.4 mmol). After 1 hour at 0° C. another 23.2 mL of the 3.0 M methylmagnesium bromide solution is added, and the suspension is allowed to come to room temperature and stirred overnight. The reaction is quenched with 100 mL of saturated aqueous ammonium chloride, and partitioned between water and ethyl acetate. The organic layer is dried (magnesium sulfate) and concentrated to give 5.24 g (96%) of the product, mp 140-142° C.

Workup

  1. temperaturecooled by an ice bath
  2. additionis added during 20 minutes
  3. customto come to room temperature
  4. customThe reaction is quenched with 100 mL of saturated aqueous ammonium chloride
  5. custompartitioned between water and ethyl acetate
  6. dry with materialThe organic layer is dried (magnesium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d6b49a89379d4498a7a7ef4348e900a8
Source dataset
uspto-grants-2006_05
Patent number
US07053070B2

Reaction notes

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