p-Toluenesulfonic acid monohydrate → 2-[2-Chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-ol

HRID 451428Notes

Reaction equation

HRID 451428 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:16]([CH3:23])([O:18][Si](C)(C)C)[CH3:17])[N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([C:16]([OH:18])([CH3:23])[CH3:17])[CH:5]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[N:7]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 866567032-Chloro-4-(4-chloro-benzyl)-6-(1-methyl-1-trimethylsilanyloxy-ethyl)-pyrimidine

Product 1

HCID 866567012-[2-Chloro-6-(4-chloro-benzyl)-pyrimidin-4-yl]-propan-2-olYield 77%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-4-(4-chloro-benzyl)-6-(1-methyl-1-trimethylsilanyloxy-ethyl)-pyrimidine (3.69 g, 10.0 mmol) and toluene-4-sulfonic acid monohydrate (0.19 g, 1.0 mmol) in 90% aqueous tetrahydrofuran (40 mL) was stirred at 20° C. for 2 h. The solution was diluted with ethyl acetate and washed successively with saturated sodium hydrogencarbonate solution and with brine. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residual oil was crystallized from cyclohexane to give the title compound (2.28 g, 77%) as a white solid.

Workup

  1. washwashed successively with saturated sodium hydrogencarbonate solution and with brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe residual oil was crystallized from cyclohexane

Sources & evidence

ORD record
ord-6f734aee6f914c0bb343501721127eaf
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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