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Formaldehyde → 4-tert.-butyl-N-[6-(4-phenoxy-2-butynyloxy)-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide

HRID 2085110
Notes
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Reaction equation

HRID 2085110 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19](Cl)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[O:29]([CH2:36][C:37]#[C:38][CH2:39][OH:40])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(OCC#C)C=CC=CC=1.C=O.[H-].[Na+]>C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19]([O:40][CH2:39][C:38]#[C:37][CH2:36][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 83613(Prop-2-ynyloxy)benzeneHCID 160466794-Phenoxybut-2-yn-1-olHCID 227294154-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide

Product 1

HCID 10230654
4-tert.-butyl-N-[6-(4-phenoxy-2-butynyloxy)-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide
Yield 41.1%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 282 mg of 4-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide (Example 12c) and 1.10 g of 4-phenoxy-2-butyn-1-ol (prepared starting from phenyl-propargylether and para-formaldehyde following the procedure given in J. Chem. Soc. Perkin Trans. 1, 1991, 1721-1727) in 15 ml THF was added 271 mg of 55% NaH in mineral oil. The suspension was stirred for 4 h at reflux. The reaction mixture was cooled, diluted with 100 ml 10% aqueous citric acid and extracted 4 times with 50 ml of ethyl acetate. The combined organic phases were washed with water, dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel eluting with heptane:ethyl acetate 1:1 and precipitated from diethyl ether to give 151 mg of 4-tert.-butyl-N-[6-(4-phenoxy-2-butynyloxy)-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide as a white powder. LC-MS: tR=6.34 min, [M+1]+=542.48, [M−1]−=540.15.

Workup

  1. customprepared
  2. temperatureat reflux
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted 4 times with 50 ml of ethyl acetate
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe crude product was purified by column chromatography on silica gel eluting with heptane:ethyl acetate 1:1
  9. customprecipitated from diethyl ether

Sources & evidence

ORD record
ord-f6de9c69d6a6454a9c5cd5f56bbc0ca9
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