Formaldehyde → HCID 10189776, compound

HRID 2085106Notes

Reaction equation

HRID 2085106 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19](Cl)[N:18]=[C:17]([C:31]3[N:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[O:37]([CH2:44][C:45]#[C:46][CH2:47][OH:48])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C1(OCC#C)C=CC=CC=1.C=O.[H-].[Na+]>C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[NH3:14].[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:48][CH2:47][C:46]#[C:45][CH2:44][O:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:18]=[C:17]([C:31]3[N:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 83613(Prop-2-ynyloxy)benzeneHCID 111351604-Tert-butyl-n-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamideHCID 160466794-Phenoxybut-2-yn-1-ol

Product 2

HCID 222AmmoniaHCID 10189776HCID 10189776, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 260 mg of 4-tert.-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide (Example 5a) and 1.50 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 184 mg of 55% NaH in mineral oil. The suspension was stirred for 1 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 chromatography on prep. tlc-plates with ethyl acetate:methanol:sat. aqueous ammonia 8:2:1 to give 82 mg of 4-tert.-butyl-N-[6-(4-phenoxy-2-butynyloxy)-5-(o-methoxy-phenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide as a slightly yellow foam. LC-MS: tR=5.60 min, [M+1]+=652.63, [M−1]−=650.58.

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 chromatography on prep

Sources & evidence

ORD record
ord-35151cef3a6247ce97b9ee9824773fd6
Source dataset
uspto-grants-2004_04
Patent number
US06720322B2

Reaction notes

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