Lithium iodide → (R)-4-(2-chloro-6-(iodomethyl)pyrimidin-4-yl)-3-methylmorpholine

HRID 1465839노트

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HRID 1465839 반응식
[I-:1].[Li+].CS(O[CH2:8][C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@H:16]2[CH3:21])[N:12]=[C:11]([Cl:22])[N:10]=1)(=O)=O>O1CCOCC1>[Cl:22][C:11]1[N:12]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@H:16]2[CH3:21])[CH:14]=[C:9]([CH2:8][I:1])[N:10]=1

참가 물질

4

반응물 2

HCID 66321Lithium iodideHCID 86651636(R)-(2-chloro-6-(3-methylmorpholino)pyrimidin-4-yl)methyl methanesulfonate

생성물 1

HCID 71584551(R)-4-(2-chloro-6-(iodomethyl)pyrimidin-4-yl)-3-methylmorpholine수율 66%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

Lithium iodide (17.57 g, 131.27 mmol) was added to (R)-(2-chloro-6-(3-methylmorpholino)pyrimidin-4-yl)methyl methanesulfonate (19.2 g, 59.67 mmol) in dioxane (300 ml) and heated to 100° C. for 2 hours under nitrogen. The reaction mixture was quenched with water (200 ml) and extracted with EtOAc (3×200 ml). The organic layers were combined and washed with 2M sodium bisulfite solution (400 ml), water (400 ml), brine (400 ml) dried over MgSO4 and then evaporated. The residue was triturated with Et2O to afford (R)-4-(2-chloro-6-(iodomethyl)pyrimidin-4-yl)-3-methylmorpholine (13.89 g, 66%); 1H NMR (400 MHz, CDCl3) 1.32 (3H, d), 3.28 (1H, td), 3.54 (1H, td), 3.69 (1H, dd), 3.78 (1H, d), 3.98-4.02 (2H, m), 4.21 (2H, s), 4.29 (1H, br s), 6.41 (1H, s); m/z: (ESI+) MH+, 354.31.

후처리

  1. customThe reaction mixture was quenched with water (200 ml)
  2. extractionextracted with EtOAc (3×200 ml)
  3. washwashed with 2M sodium bisulfite solution (400 ml), water (400 ml), brine (400 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was triturated with Et2O

출처 및 근거

ORD 기록
ord-779c2140ade7478b86ddcae4ce713995
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999997B2

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