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

HRID 2227824노트

반응식

HRID 2227824 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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, 2.43 g (77%). 1H NMR (CDCl3, 300 MHz) δ1.82 (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+).

후처리

  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

출처 및 근거

ORD 기록
ord-215f22bf24d84ff48fe4ce118ab5e017
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06414149B1

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