Ethanol → (5-Bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine

HRID 910202

Reaction equation

HRID 910202 reaction equation
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1.C(O)C.C(N(CC)CC)C.[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>O>[Br:1][C:2]1[C:10]2[C:9]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[N:8][CH:7]=[N:6][C:5]=2[S:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 454802995-Bromo-4-chlorothieno[2,3-d]pyrimidine

Product 1

HCID 67381984(5-Bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamineYield 63.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 5-bromo-4-chlorothieno[2,3-d]pyrimidine (3.8 g, 15.2 mmol), ethanol (250 ml), triethylamine (2.32 ml, 16.7 mmol) and 2-aminomethylpyridine (1.72 ml, 16.7 mmol) was heated under reflux for 2.5 hours. The solution was then cooled to ambient temperature, poured into water (300 ml) and extracted with dichloromethane (3×150 ml). The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude product. Purification by flash chromatography (silica) eluting with ethyl acetate and 40°-60° petroleum ether (1:1) gave (5-bromothieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine as a yellow solid (3.12 g), m.pt. 127°-129° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. extractionextracted with dichloromethane (3×150 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give the crude product
  7. customPurification by flash chromatography (silica)
  8. washeluting with ethyl acetate and 40°-60° petroleum ether (1:1)

Sources & evidence

ORD record
ord-71d2c6e6e7b84271b2054899a74236be
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Linked notes

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