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Dimethyl Sulfoxide → n-(2-{[4-(2,4-Dichlorophenyl)-5-formylpyrimidin-2-yl]amino}ethyl)(tert-butoxy)-carboxamide

HRID 1825536
Notes
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Reaction equation

HRID 1825536 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:10]=1.C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH:15]=[O:16])=[CH:13][N:12]=[C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22142949n-(2-{[4-(2,4-Dichlorophenyl)-5-(hydroxymethyl)pyrimidin-2-yl]amino}ethyl)(tert-butoxy)carboxamide

Product 1

HCID 22142985n-(2-{[4-(2,4-Dichlorophenyl)-5-formylpyrimidin-2-yl]amino}ethyl)(tert-butoxy)-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Using the method of Swern, et al., 100 mg of N-(2-{[4-(2,4-dichlorophenyl)-5-(hydroxymethyl)pyrimidin-2-yl]amino}ethyl)(tert-butoxy)carboxamide was dissolved in 1 mL of anhydrous methylene chloride and added to a solution of oxalyl chloride (30.7 μL, 0.363 mmol) and DMSO (51.6 μL, 0.726 mmol) which had been stirring at −78° C. for 15 min. The resulting solution was stirred for an additional 30 min, at which time 202 μL (1.45 mmol) of triethyl amine was added. The resulting suspension was allowed to warm to room temperature after 15 min and 1 mL of water was added and the layers separated. The aqueous layer was extracted with methylene chloride and the combined organic layers dried (sodium sulfate) and concentrated to afford N-(2-{[4-(2,4-dichlorophenyl)-5-formylpyrimidin-2-yl]amino}ethyl)(tert-butoxy)carboxamide as a light yellow foam. This product proved to be air sensitive and was used without further manipulation.

Workup

  1. additionwas added
  2. temperatureto warm to room temperature after 15 min
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. dry with materialthe combined organic layers dried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-571495e464d14bb5887da858b6520b00
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07045519B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes