Tetrahydrofuran → HCID 86632016, compound

HRID 419724Notes

Reaction equation

HRID 419724 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[CH2:11]([Mg]Br)[CH3:12].C1COCC1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:11][CH3:12])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 86632016HCID 86632016, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

Charge 4,6-dichloro-pyrimidine-5-carbaldehyde (2.5 g, 1.0 eq) and toluene (50 mL) in a round bottom flask. Cool the reaction mass to −10° C. Add ethyl magnesium bromide (3M) in THF solution (5.1 mL, 1.1 eq) drop wise at −10° C. Slowly allow the reaction mass to come to RT in 1 h. Charge chilled ammonium chloride solution to the reaction mass and extract with diethyl ether. Wash ether layer with saturated aq. sodium chloride solution. Dry the ether layer over anhydrous sodium sulfate and concentrated it under reduced pressure to get the desired product (2.3 g, 79.3%).

Workup

  1. customwise at −10° C
  2. additionCharge
  3. extractionextract with diethyl ether
  4. dry with materialDry the ether layer over anhydrous sodium sulfate
  5. concentrationconcentrated it under reduced pressure

Sources & evidence

ORD record
ord-a9f045c942f542ef89927787458e017d
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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