Sodium Hydroxide → 2-Hydroxymethyl-4-(4-(N,N-dimethylaminosulfonyl)-1-piperazino)pyrimidine

HRID 1586705Notes

Reaction equation

HRID 1586705 reaction equation
[CH3:1][N:2]([CH3:21])[S:3]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH2:18][O:19]C)[N:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4].B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[CH3:1][N:2]([CH3:21])[S:3]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH2:18][OH:19])[N:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 14988722HCID 14988722, compound

Product 1

HCID 1323022-Hydroxymethyl-4-(4-(N,N-dimethylaminosulfonyl)-1-piperazino)pyrimidineYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

11.0 g (35 mmol) of 4-[4-(N,N-dimethylsulfamoyl)piperazino]-2-methyloxymethylpyrimidine (Example 1) are dissolved in 45 ml of dry methylene chloride. Between 0° C. and +5° C., 13.2 g (52.5 mmol) of boron tribromide dissolved in 25 ml of methylene chloride are slowly added dropwise under argon. The mixture is stirred for a further 1.5 h while cooling in ice and is hydrolyzed with cold 2 N sodium hydroxide solution. The organic phase is separated off, and the aqueous phase is extracted 3 times more with methylene chloride. The combined organic phases are washed with saturated ammonium chloride solution, water and saturated sodium chloride solution and dried over sodium sulfate and the solvent is removed in vacuo. Crystallization of the residue in butyl acetate results in 7.60 g of solid product of melting point 148°-149° C.

Workup

  1. additionare slowly added dropwise under argon
  2. temperaturewhile cooling in ice
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted 3 times more with methylene chloride
  5. washThe combined organic phases are washed with saturated ammonium chloride solution, water and saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed in vacuo
  8. customCrystallization of the residue in butyl acetate

Sources & evidence

ORD record
ord-c28ee0ca11424f18a88ec6e41b3080ba
Source dataset
uspto-grants-1993_06
Patent number
US05215990

Reaction notes

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