Methylamine → N-methyl-2-{5-phenyl-4-[{pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetamide

HRID 910196Notes

Reaction equation

HRID 910196 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:7]=[C:8]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][S:12][C:10]=2[N:11]=1)C.[CH3:30][NH2:31]>C(O)C.O>[CH3:30][NH:31][C:4](=[O:3])[CH2:5][C:6]1[N:7]=[C:8]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][S:12][C:10]=2[N:11]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 11711155(5-Phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetic acid ethyl ester

Product 1

HCID 11417887N-methyl-2-{5-phenyl-4-[{pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a 10 ml glass tube were placed (5-phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetic acid ethyl ester (35 mg, 0.088 mmol) and a saturated solution of methylamine in ethanol (2.0 ml). The tube was sealed with a septum and placed in the microwave cavity. Microwave irradiation of 200 W was used, the temperature being ramped from room temperature to 100° C. Once 100° C. was reached, the reaction mixture was held at this temperature for 30 minutes. The temperature was then ramped up to 150° C. and the reaction mixture was held at this temperature for a further 30 minutes. The resultant mixture was diluted with water (50 ml) and extracted with dichloromethane (3×50 ml). The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give a residue which was purified by flash chromatography (silica) eluting with 5% methanol in dichloromethane to give N-methyl-2-{5-phenyl-4-[{pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetamide (2 mg).

Workup

  1. customIn a 10 ml glass tube were placed
  2. customThe tube was sealed with a septum
  3. customMicrowave irradiation of 200 W
  4. custombeing ramped from room temperature to 100° C
  5. customOnce 100° C.
  6. customwas then ramped up to 150° C.
  7. waitthe reaction mixture was held at this temperature for a further 30 minutes
  8. extractionextracted with dichloromethane (3×50 ml)
  9. dry with materialThe combined organic extracts were dried (MgSO4)
  10. customthe solvent removed in vacuo
  11. customto give a residue which
  12. customwas purified by flash chromatography (silica)
  13. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-45c7d12cb4544e5481f0896aab46721f
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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