N,N-Dimethylethylenediamine → HCID 67388435, compound

HRID 269838Notes

Reaction equation

HRID 269838 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=3)[C:14]([C:25]([OH:27])=O)=[CH:13][N:12]=2)=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH3:50][N:51]([CH3:55])[CH2:52][CH2:53][NH2:54]>O.CN(C=O)C>[CH3:50][N:51]([CH3:55])[CH2:52][CH2:53][NH:54][C:25]([C:14]1[C:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)=[N:16][C:11]([NH:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[N:12][CH:13]=1)=[O:27]

Participants

7

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67388725HCID 67388725, compound

Product 1

HCID 67388435HCID 67388435, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A 4 ml portion of DMF solution containing 352 mg of 2-{[2-(4-hydroxyphenyl)ethyl]amino}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxylic acid was mixed with 223 mg of WSC hydrochloride, 157 mg of HOBt and 103 mg of 2-dimethylaminoethylamine, followed by stirring overnight at room temperature. The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was washed with saturated brine and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (chloroform:methanol:aqueous ammonia) and then recrystallized (hexane-ethyl acetate) to obtain 291 mg of N-(2-dimethylaminoethyl)-2-{[2-(4-hydroxyphenyl)ethyl]amino}-4-[(3-methylphenyl)amino]pyrimidine-5-carboxamide as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. customThe resulting residue was purified by a silica gel column chromatography (chloroform:methanol:aqueous ammonia)
  5. customrecrystallized (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-fab4571a91004211a7daaf8e5fb90c1c
Source dataset
uspto-grants-2008_11
Patent number
US07449456B2

Reaction notes

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