Trimethylamine → 3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-cyclopropylbenzamide

HRID 2042220Notes

Reaction equation

HRID 2042220 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=3)[C:14]([OH:16])=O)[C:6]=2[N:7]=1.[CH:20]1([NH2:23])[CH2:22][CH2:21]1.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.CN(C)C>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=3)[C:14]([NH:23][CH:20]3[CH2:22][CH2:21]3)=[O:16])[C:6]=2[N:7]=1

Participants

8

Reactant 5

HCID 1146TrimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 866732193-(2-Chlorothieno[3,2-d]pyrimidin-7-yl)benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 866732203-(2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-cyclopropylbenzamideYield 85.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Chlorothieno[3,2-d]pyrimidin-7-yl)benzoic acid (600 mg, 2.06 mmol) was dissolved in N,N-dimethylformamide (20 mL) and then cyclopropylamine (234 mg, 4.12 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (589 mg, 3.09 mmol), hydroxybenzotriazole (417 mg, 3.09 mmol) and trimethylamine (574 mL, 4.12 mmol) were added. The reaction mixture was stirred at room temperature for a day, diluted with ethyl acetate, and washed with ammonium chloride aqueous solution. The organic layer was dried with magnesium sulfate, filtered with celite, and then concentrated. Purification by chromatography (20% ethyl acetate/hexane) yielded the target compound (580 mg, 85% yield).

Workup

  1. washwashed with ammonium chloride aqueous solution
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered with celite
  4. concentrationconcentrated
  5. customPurification by chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-26d2ee2c846c4598bca5f3c8b17cfb34
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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