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Sodium hydride → (5-Chlorothieno[2,3-d]pyrimidin-4-yl)-{2-[3-methoxy-4-(4-trifluoromethylpyridin-2-yloxy)phenyl]ethyl}amine

HRID 491264
Notes
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Reaction equation

HRID 491264 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:12]2[C:11]([NH:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=3)=[N:10][CH:9]=[N:8][C:7]=2[S:6][CH:5]=1.Cl[C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][N:27]=1>CS(C)=O.O>[Cl:3][C:4]1[C:12]2[C:11]([NH:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:26]4[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][N:27]=4)=[C:18]([O:23][CH3:24])[CH:17]=3)=[N:10][CH:9]=[N:8][C:7]=2[S:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1449582-Chloro-4-(trifluoromethyl)pyridineHCID 688569804-[2-(5-Chlorothieno[2,3-d]pyrimidin-4-ylamino)ethyl]-2-methoxyphenol

Product 1

HCID 57677118(5-Chlorothieno[2,3-d]pyrimidin-4-yl)-{2-[3-methoxy-4-(4-trifluoromethylpyridin-2-yloxy)phenyl]ethyl}amineYield 33%

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 60 percent sodium hydride / oil dispersion (31 mg, 0.78 mmol) in DMSO (3 mL) was added 4-{2-[(5-chlorothieno[2,3-d]pyrimidin-4-yl)amino]ethyl}-2-methoxyphenol (250 mg, 0.75 mmol). After stirring for 30 min, 2-chloro-4-(trifluoromethyl)pyridine (141 mg, 0.78 mmol) was added and the reaction heated at 80° C. overnight. The reaction mixture was diluted with H2O and the precipitate collected by filtration. The filter cake washed with H2O and then dissolved in CH2Cl2. The organics were dried with (Na2SO4), filtered and the stripped in vacuo. The solid residue was triturated with a mixture of ether and pentane leaving a brown solid, 120 mg, 0.25 mmol, 33 percent yield.

Workup

  1. filtrationthe precipitate collected by filtration
  2. washThe filter cake washed with H2O
  3. dissolutiondissolved in CH2Cl2
  4. dry with materialThe organics were dried with (Na2SO4)
  5. filtrationfiltered
  6. customThe solid residue was triturated with a mixture of ether and pentane leaving a brown solid, 120 mg, 0.25 mmol, 33 percent yield

Sources & evidence

ORD record
ord-d8bd4739416f4aeeabad4d66d2a02228
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531482B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes