Ethanolamine → HCID 10268808, compound

HRID 131194Notes

Reaction equation

HRID 131194 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[C:8](Cl)[N:9]=[C:10]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[C:5]=2[S:4][CH:3]=1.[CH2:17]([CH2:19][NH2:20])[OH:18].O>CN1CCCC1=O>[Br:1][C:2]1[C:6]2[N:7]=[C:8]([NH:20][CH2:19][CH2:17][OH:18])[N:9]=[C:10]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[C:5]=2[S:4][CH:3]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 962WaterHCID 59732317HCID 59732317, compound

Product 1

HCID 10268808HCID 10268808, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 7-bromo-2-chloro-4-(2-furyl)thieno[3,2-d]pyrimidine (110 mg, 0.35 mmol) in 1-methyl-2-pyrrolidinone (1 mL) was treated with ethanolamine (32 μL, 0.52 mmol), heated at 90° C. for 16 h, cooled, poured into water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo and purified by chromatography (SiO2: EtOAc:Heptane, 1:1) to give the title compound (45 mg, 38%) as a yellow solid.

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography (SiO2: EtOAc:Heptane, 1:1)

Sources & evidence

ORD record
ord-a6aa5b6c1f8a4bfebab2c4a9bac7cf91
Source dataset
uspto-grants-2008_06
Patent number
US07384949B2

Reaction notes

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