Boron tribromide → {4-[4-(Pyrrolidine-1-sulfonyl)-piperazin-1-yl]-pyrimidin-2-yl}-methanol

HRID 586177Notes

Reaction equation

HRID 586177 reaction equation
C[O:2][CH2:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)[CH:7]=[CH:6][N:5]=1.B(Br)(Br)Br>ClCCl>[N:19]1([S:16]([N:13]2[CH2:12][CH2:11][N:10]([C:8]3[CH:7]=[CH:6][N:5]=[C:4]([CH2:3][OH:2])[N:9]=3)[CH2:15][CH2:14]2)(=[O:18])=[O:17])[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 223287382-Methoxymethyl-4-[4-(pyrrolidine-1-sulfonyl)-piperazin-1-yl]-pyrimidine

Product 1

HCID 22328774{4-[4-(Pyrrolidine-1-sulfonyl)-piperazin-1-yl]-pyrimidin-2-yl}-methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxymethyl-4-[4-(pyrrolidine-1-sulfonyl)-piperazin-1-yl]-pyrimidine (prepared according to the method of Example 121, Step A, 3.1 g, 9.4 mmol) in dichloromethane (47 mL) was added boron tribromide (1 M in dichloromethane, 19 mL, 18.7 mmol) at 0° C. then stirred at ambient temperature for 2 h. The mixture was washed twice with saturated aqueous sodium bicarbonate, and the organic layer was separated, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give an oil which was crystallized from isopropyl ether to give the title compound as a white solid, 2.431 g (77%). 1H NMR (CDCl3, 300 MHz) δ 1.82 (m, 4H), 3.15 (m, 8H), 3.81 (m, 4H), 4.35 (d, 2H), 4.83 (t, 1H), 6.71 (d, 1H), 8.18 (d, 1H); mp: 128-131° C.; MS (CI) 328 (MH+).

Workup

  1. washThe mixture was washed twice with saturated aqueous sodium bicarbonate
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customto give an oil which
  7. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-86e72b0216a14333bb12c9a8ca0ebdd3
Source dataset
uspto-grants-2005_08
Patent number
US06936600B2

Reaction notes

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