Lithium Hexamethyldisilazide → HCID 67326011, compound

HRID 333720Notes

Reaction equation

HRID 333720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([C:15]#[N:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C[Si](C)(C)[N-:19][Si](C)(C)C.[Li+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([C:15]([NH2:19])=[NH:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 67325961HCID 67325961, compound

Product 1

HCID 67326011HCID 67326011, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Referring to Reaction Scheme 4, Stage 1, to a stirred solution of 6-(3,4-dichloro-phenyl)-pyrimidine-4-carbonitrile (1 eq) in anhydrous toluene (20 vol) at 0° C. was added lithium hexamethyldisilazide (2 eq) and the reaction mixture was stirred at ambient temperature for 2 hours under an atmosphere of nitrogen. The reaction mixture was cooled to 0° C. and quenched with HCl (3M). After 30 minutes stirring, water (40 vol) was added, followed by toluene (20 vol). The mixture was partitioned and the precipitate present in the aqueous phase was filtered off. The solid was suspended in a 3M solution of sodium hydroxide, stirred at room temperature for 30 minutes to give 6-(3,4-dichloro-phenyl)-pyrimidine-4-carboxamidine, which was used in the next stage without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with HCl (3M)
  3. stirringAfter 30 minutes stirring
  4. additionwater (40 vol) was added
  5. customThe mixture was partitioned
  6. filtrationthe precipitate present in the aqueous phase was filtered off
  7. stirringstirred at room temperature for 30 minutes

Sources & evidence

ORD record
ord-9e12fc50fab445fa9856d4c58b2e7677
Source dataset
uspto-grants-2014_11
Patent number
US08883785B2

Reaction notes

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