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Water → 4-tert.-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)4-pyrimidinyl]-benzene sulfonamide

HRID 2085078
Notes
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Reaction equation

HRID 2085078 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:3]=1.[K+].[C:25]([C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH-:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26].O.C(OCC)C>CN(C=O)C.C(O)(=O)C>[C:25]([C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:38][C:2]2[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[N:3]=2)(=[O:36])=[O:37])=[CH:31][CH:30]=1)([CH3:28])([CH3:26])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 111754584,6-Dichloro-5-(2-methoxyphenoxy)-2-(pyridin-4-YL)pyrimidineHCID 131721323HCID 131721323, compound

Product 1

HCID 190957714-tert.-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)4-pyrimidinyl]-benzene sulfonamide

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.1 g of 4,6-dichloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (Example 1, Section a) to d)) in 100 ml of dry DMF 8.8 g of 4-tert.-butyl benzene sulfonamide potassium salt was added at room temperature. The solution was stirred over night at room temperature. The solution was added to a mixture of 150 ml of water and 100 ml of diethyl ether. The pH was adjusted to 5 by adding acetic acid. The precipitate that formed was collected, washed with water and diethyl ether. The resulting powder was suspended in boiling ethyl acetate. The mixture was allowed to cool in an icebath. Eventually, the solid material was collected and dried to yield 6.6 g of 4-tert.-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)4-pyrimidinyl]-benzene sulfonamide as beige crystals. LC-MS: tR=5.80 min, [M+1]+=525.31, [M−1]−=523.48.

Workup

  1. customThe precipitate that formed
  2. customwas collected
  3. washwashed with water and diethyl ether
  4. temperatureto cool in an icebath
  5. customEventually, the solid material was collected
  6. customdried

Sources & evidence

ORD record
ord-d41a8b84804847d8b28c5ab86cb9f656
Source dataset
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06720322B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes