Lithium Hexamethyldisilazide → N-[2-(benzyloxy)pyrimidin-4-yl]-5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluorobenzenesulfonamide

HRID 337983Notes

Reaction equation

HRID 337983 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:27][C:28]1[C:29]([F:39])=[CH:30][C:31]([F:38])=[C:32]([S:34](Cl)(=[O:36])=[O:35])[CH:33]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[CH2:1]([O:8][C:9]1[N:14]=[C:13]([N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[S:34]([C:32]2[CH:33]=[C:28]([Cl:27])[C:29]([F:39])=[CH:30][C:31]=2[F:38])(=[O:36])=[O:35])[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 27735275-Chloro-2,4-difluorobenzenesulphonyl chlorideHCID 899628682-(Benzyloxy)-N-(2,4-dimethoxybenzyl)pyrimidin-4-amine

Product 1

HCID 89962786N-[2-(benzyloxy)pyrimidin-4-yl]-5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluorobenzenesulfonamideYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 86a by using the 2-(benzyloxy)-N-(2,4-dimethoxybenzyl)pyrimidin-4-amine (0.50 g, 1.42 mmol) prepared in Example 153a, 5-chloro-2,4-difluorobenzenesulfonyl chloride (0.36 g, 1.57 mmol), lithium bis(trimethylsilyl)amide (1.0 M solution in THF; 1.71 mL, 1.71 mmol) and THF (5.0 mL), to yield the title compound (487.8 mg, 61%) as a colorless solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-d95dfe8df5824bbebcbf2c6d00aa4f43
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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