Methanesulfonyl chloride → 2-Amino-5-(4-(chloromethyl)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

HRID 2207063Notes

Reaction equation

HRID 2207063 reaction equation
CS([Cl:5])(=O)=O.[Cl-].[Li+].[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[S:17]([O:20][C:21]1[C:26]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34]O)=[CH:30][C:29]=2[O:36][CH3:37])=[C:25]([CH3:38])[N:24]=[C:23]([NH2:39])[N:22]=1)(=[O:19])=[O:18]>C1COCC1.O>[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[S:17]([O:20][C:21]1[C:26]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][Cl:5])=[CH:30][C:29]=2[O:36][CH3:37])=[C:25]([CH3:38])[N:24]=[C:23]([NH2:39])[N:22]=1)(=[O:19])=[O:18]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 879451512-Amino-5-(4-(hydroxymethyl)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 879450752-Amino-5-(4-(chloromethyl)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (1.4 mL) was added to a mixture of lithium chloride (0.74 g) and the product from step (iv) (4.0 g) in THF (45 mL). The mixture was stirred at RT for 1.5 h, diluted with water and extracted with EtOAc. The combined organic layer was washed with brine, dried and concentrated under reduced pressure to afford the crude product as a pale yellow oil, which was used for next reaction without further purification; 1H NMR (300 MHz, CDCl3); 6.91 (2H, s), 6.83 (1H, s), 6.81-6.74 (2H, m), 4.69 (2H, br s), 4.54 (2H, s), 3.82 (3H, s), 3.80 (2H, s), 2.54 (6H, s), 2.29 (3H, s), 2.24 (3H, s).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b1116549723432e9a4589bf703868a3
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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