Sodium hydride → 5-tert-Butyl-N-[6-methoxy-5-(2-methoxy-phenoxy)-2,2'-bipyrimidin-4-yl]-thiophene-2-sulphonamide

HRID 356645Notes

Reaction equation

HRID 356645 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[C:8]([O:19][CH3:20])[N:7]=[C:6]([C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[N:5]=1.[C:27]([C:31]1[S:35][C:34]([S:36](Cl)(=[O:38])=[O:37])=[CH:33][CH:32]=1)([CH3:30])([CH3:29])[CH3:28]>O1CCCC1>[C:27]([C:31]1[S:35][C:34]([S:36]([NH:3][C:4]2[C:9]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[C:8]([O:19][CH3:20])[N:7]=[C:6]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[N:5]=2)(=[O:38])=[O:37])=[CH:33][CH:32]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 218455645-Tert-butylthiophene-2-sulfonyl chlorideHCID 229997224-Amino-6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine

Product 1

HCID 189389185-tert-Butyl-N-[6-methoxy-5-(2-methoxy-phenoxy)-2,2'-bipyrimidin-4-yl]-thiophene-2-sulphonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

92 mg of NaH (65%) were added at room temperature to a solution of 162.5 mg of 4-amino-6-methoxy-5-(2-methoxy-phenoxy)-2,2'-bipyrimidine in 10 ml of tetrahydrofuran, the solution was stirred at room temperature for 11/2 hours and subsequently 162.5 mg of 5-tert-butyl-thiophene-2-sulphonyl chloride were added at the same temperature. The mixture was stirred at room temperature for a further 2 hours, poured on to ice/water, extracted with ethyl acetate, the aqueous phase was acidified and extracted with methylene chloride. The combined, organic phases were dried over magnesium sulphate and concentrated on a rotary evaporator. The residue was chromatographed over silica gel with methylene chloride/methanol (20/1) as the eluent. 5-tert-Butyl-N-[6-methoxy-5-(2-methoxy-phenoxy)-2,2'-bipyrimidin-4-yl]-thiophene-2-sulphonamide was obtained as a yellow powder. MS: 463 (M-SO2).

Workup

  1. additionwere added at the same temperature
  2. extractionextracted with ethyl acetate
  3. extractionextracted with methylene chloride
  4. dry with materialorganic phases were dried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue was chromatographed over silica gel with methylene chloride/methanol (20/1) as the eluent

Sources & evidence

ORD record
ord-3565077d924348598dab78058302ab8f
Source dataset
uspto-grants-1998_11
Patent number
US05837708

Reaction notes

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