Methyl iodide → HCID 10296752, 화합물

HRID 855630노트

반응식

HRID 855630 반응식
[CH3:1][N:2]([C:21]1[CH:29]=[C:28]2[C:24]([C:25]([CH3:30])=[N:26][NH:27]2)=[CH:23][CH:22]=1)[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:11]=2)[N:4]=1.[C:31]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C.O>[CH3:31][N:27]1[C:28]2[C:24](=[CH:23][CH:22]=[C:21]([N:2]([CH3:1])[C:3]3[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:11]=4)[N:4]=3)[CH:29]=2)[C:25]([CH3:30])=[N:26]1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178434348HCID 178434348, 화합물

생성물 1

HCID 10296752HCID 10296752, 화합물수율 64.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of N4-methyl-N4-(3-methyl-1H-indazol-6-yl)-N2-{3-[(methylsulfonyl)methyl]phenyl}-2,4-pyrimidinediamine (Example 23) (389 mg, 0.92 mmol) in DMF (4 ml) was added Cs2CO3 (600 mg, 1.84 mmol) followed by iodomethane (64 ul, 1.02 mmol). The mixture was stirred at rt overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated. Purification of crude product by prep TLC provided 260 mg of N4-(1,3-dimethyl-1H-indazol-6-yl)-N4-methyl-N2-{3-[(methylsulfonyl)methyl]-phenyl}-2,4-pyrimidinediamine. 1H NMR (300 MHz, d6DMSO) δ 9.25 (s, 1H), 7.86 (d, J=6.0 Hz, 1H), 7.82 (s, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.65 (d, J=7.8 Hz, 1H), 7.58 (s, 1H), 7.15 (t, J=7.8 Hz, 1H), 7.02 (d, J=8.5 Hz, 1H), 6.89 (d, J=7.8 Hz, 1H), 5.83 (d, J=6.0 Hz, 1H), 4.28 (s, 2H), 3.92 (s, 3H), 3.49(s, 3H), 2.87 (s, 3H), 2.48 (s, 3H). MS (ES+, m/z) 437 (M+H).

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification of crude product by prep TLC

출처 및 근거

ORD 기록
ord-934c761a694d44309ffeed9f2b155132
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262203B2

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