Trimethylamine → 3-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamide

HRID 1485488Notes

Reaction equation

HRID 1485488 reaction equation
[NH2:1][C:2]1[C:3]2[S:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([OH:17])=O)[C:4]=2[N:5]=[C:6]([Cl:8])[N:7]=1.Cl.CN.[CH2:24]([N:26]=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.CN(C)C>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]2[S:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([NH:26][CH3:24])=[O:17])[C:4]=2[N:5]=[C:6]([Cl:8])[N:7]=1

Participants

8

Reactant 5

HCID 1146TrimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6364545Methylamine hydrochlorideHCID 866756513-(4-Amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 866756523-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzamideYield 89.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)benzoic acid (300 mg, 0.98 mmol) was dissolved in N,N-dimethylformamide (5 mL) and then methylamine hydrochloride (329 mg, 4.91 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (282 mg, 1.47 mmol), hydroxybenzotriazole (239 mg, 1.76 mmol) and trimethylamine (0.889 mL, 6.38 mmol) were added. The reaction mixture was stirred at room temperature for a day. The reaction mixture was diluted with ethyl acetate and then washed with ammonium chloride aqueous solution. The organic layer was dried with magnesium sulfate, filtered with celite and then concentrated. Purification by chromatography (1/4 ethyl acetate/hexane) yielded the target compound (280 mg, 89% 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 (1/4 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cddbe8c3fc1f4e6f89228ca4466d3637
Source dataset
uspto-grants-2016_08
Patent number
US09422307B2

Reaction notes

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