Diisopropylethylamine → 6-[(5-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoic acid methyl ester

HRID 1926873Notes

Reaction equation

HRID 1926873 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][O:8][C:4]=2[N:5]=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.Cl.[CH3:27][O:28][C:29](=[O:36])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35]>CN(C=O)C>[CH3:27][O:28][C:29](=[O:36])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11499324Methyl 6-aminohexanoate hydrochlorideHCID 594278334-Chloro-5-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 580169256-[(5-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Heat 500 mg (2.19 mmol) 4-chloro-5-phenylfuro[2,3-d]pyrimidine, 1.51 ml (8.67 mmol) DIEA and 1 ml DMF to 160° C. and add 787.6 mg (4.34 mmol) 6-aminohexanoic acid methyl ester hydrochloride. After 4 h at 160° C., cool the reaction mixture, add to ice water and extract three times with ethyl acetate. Combine the organic phases and wash with saturated ammonium chloride solution, dry over magnesium sulphate and concentrate under vacuum. Purify the residue by chromatography on silica gel (solvent: cyclohexane/ethyl acetate 10:1→3:1). 470 mg (63.9% of theor.) of the target compound is obtained.

Workup

  1. temperaturecool the reaction mixture
  2. extractionextract three times with ethyl acetate
  3. washwash with saturated ammonium chloride solution
  4. dry with materialdry over magnesium sulphate
  5. concentrationconcentrate under vacuum
  6. customPurify the residue by chromatography on silica gel (solvent: cyclohexane/ethyl acetate 10:1→3:1)
  7. custom470 mg (63.9% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-1822757d2f8f48f4a5dea003ec278e57
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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