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5-Chloropyrimidine → HCID 178461721, compound

HRID 1046427
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Reaction equation

HRID 1046427 reaction equation
OC(C(F)(F)F)=O.[CH3:8][C:9]([CH3:36])([CH3:35])[C:10]#[C:11][C:12]1[S:16][C:15]([C:17]([OH:19])=[O:18])=[C:14]([N:20]([C@@H:30]([CH3:34])[CH2:31][CH2:32][OH:33])[C:21]([C@H:23]2[CH2:28][CH2:27][C@H:26]([CH3:29])[CH2:25][CH2:24]2)=[O:22])[CH:13]=1.Cl[C:38]1[CH:39]=[N:40][CH:41]=[N:42][CH:43]=1.C(O[K])(C)(C)C>CS(C)=O>[CH3:36][C:9]([CH3:35])([CH3:8])[C:10]#[C:11][C:12]1[S:16][C:15]([C:17]([OH:19])=[O:18])=[C:14]([N:20]([C:21]([C@H:23]2[CH2:28][CH2:27][C@H:26]([CH3:29])[CH2:25][CH2:24]2)=[O:22])[C@@H:30]([CH3:34])[CH2:31][CH2:32][O:33][C:38]2[CH:39]=[N:40][CH:41]=[N:42][CH:43]=2)[CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 126003845-Chloropyrimidine3×HCID 178418922HCID 178418922, compound3×HCID 178461722HCID 178461722, compound

Product 1

HCID 178461721HCID 178461721, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 5-(3,3-dimethyl-but-1-ynyl)-3-[(3-hydroxy-1-(S)-methyl-propyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid TFA salt (100 mg, 0.239 mmol) and 5-chloro-pyrimidine (137 mg, 1.194 mmol) were dissolved in DMSO (2 mL). To this solution tBuOK (107 mg, 0.956 mmol) was added in one portion at rt. The reaction was allowed to stir at rt for 1 h and then heated to 60° C. for 1.5 h. Additional tBuOK (50 mg) and 5-chloro-pyrimidine (69 mg) were added and the reaction was run at 60° C. for another 1 h. The reaction was then heated to 100° C. for another 1 h. Additional tBuOK (50 mg) and 5-chloro-pyrimidine (69 mg) were added and the reaction was run at 100° C. overnight. The reaction was cooled to rt and quenched with a 20% (v/v) solution of acetic acid in water. The reaction was diluted with MeOH and 5-(3,3-dimethyl-but-1-ynyl)-3-{(trans-4-methyl-cyclohexanecarbonyl)-[1-(S)-methyl-3-(pyrimidin-5-yloxy)-propyl]-amino}-thiophene-2-carboxylic acid (4 mg, 2.7%) was isolated by reverse phase HPLC as the TFA salt.

Workup

  1. temperatureheated to 60° C. for 1.5 h
  2. waitthe reaction was run at 60° C. for another 1 h
  3. temperatureThe reaction was then heated to 100° C. for another 1 h
  4. waitthe reaction was run at 100° C. overnight
  5. temperatureThe reaction was cooled to rt
  6. customquenched with a 20% (v/v) solution of acetic acid in water
  7. additionThe reaction was diluted with MeOH

Sources & evidence

ORD record
ord-539b1c7f3f174beb93b637d0ff4aa3f6
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08569302B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes