Ethanol → HCID 86596371, compound

HRID 910204Notes

Reaction equation

HRID 910204 reaction equation
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][C:7]([Cl:12])=[N:6][C:5]=2[S:4][C:3]=1[CH3:13].C(O)C.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(N(CC)CC)C>O>[Br:1][C:2]1[C:10]2[C:9]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[N:8][C:7]([Cl:12])=[N:6][C:5]=2[S:4][C:3]=1[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 86017644HCID 86017644, compound

Product 1

HCID 86596371HCID 86596371, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 5-bromo-2,4-dichloro-6-methylthieno[2,3-d]pyrimidine (1.0 g, 3.35 mmol), ethanol (40 ml), 2-aminomethylpyridine (0.40 ml, 3.69 mmol) and triethylamine (0.50 ml, 3.69 mmol) was heated at a temperature of 60° C. for 1 hour. The reaction mixture was then cooled to ambient temperature, diluted with water (100 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. Purification by flash chromatography (silica) eluting with dichloromethane followed by 5% ethyl acetate in dichloromethane gave (5-bromo-2-chloro-6-methylthieno[2,3-d]pyrimidin-4-yl)pyridin-2-ylmethylamine as a white solid (0.99 g).

Workup

  1. temperatureThe reaction mixture was then cooled to ambient temperature
  2. extractionextracted with dichloromethane (3×50 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto give a residue
  6. customPurification by flash chromatography (silica)
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-e7a7242b695e4e80b7801a18a7ddc4ff
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

Loading…