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Diisopropylethylamine → HCID 86729624, compound

HRID 2284898
Notes
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Reaction equation

HRID 2284898 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:12])[CH:10]=[CH2:11].CCN(C(C)C)C(C)C.[Cl:22][C:23]1[N:28]=[C:27](Cl)[C:26]([Cl:30])=[CH:25][N:24]=1.C(OCC)(=O)C.CCCCCC>CN1C(=O)CCC1.C(OCC)(=O)C>[Cl:22][C:23]1[N:28]=[C:27]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9](=[O:12])[CH:10]=[CH2:11])[C:26]([Cl:30])=[CH:25][N:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 21226206Ethyl acetate hexaneHCID 43600040HCID 43600040, compound

Product 1

HCID 86729624HCID 86729624, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 8857
Ethyl Acetate
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of N-(2-aminophenyl)acrylamide (TFA salt) (10 g, 38.6 mmol) in N-methyl pyrrolidinone (30 mL) was added DIPEA (12.6 g, 98.36 mmol), and 2,4,5-trichloropyrimidine (9.5 g, 49.18 mmol), and the mixture was stirred at rt for 16 h. TLC showed completion of starting material (TLC system: 50% ethyl acetate/hexane, (Rf): 0.5). The reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (3×50 mL). The organic layer was separated, dried over sodium sulfate and concentrated to obtain the crude compound (11 g). MS m/z: 309.1 (ES+, M+1).

Workup

  1. washwashed with water (3×50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6f6fee94b7b64924b6eaa840c6ad85df
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145387B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes