Triethylamine → HCID 58629004, compound

HRID 1678052Notes

Reaction equation

HRID 1678052 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:7]=2[C:6]=1[OH:15])=[O:4].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([NH2:26])[CH3:25])=[CH:20][CH:19]=1.[CH2:27](N(CC)CC)C>CN(C=O)C.O>[CH2:1]([O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:26][CH:24]([C:21]3[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[CH3:25])[C:7]=2[C:6]=1[OH:15])=[O:4])[CH3:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2381811-(4-Methoxyphenyl)ethanamineHCID 86604627HCID 86604627, compound

Product 1

HCID 58629004HCID 58629004, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 4-chloro-5-hydroxythieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (0.5 g, 1.9 mol), 1-(4-methoxyphenyl)ethylamine (0.4 g, 2.5 mol) and triethylamine (1 mL) in DMF (20 mL) was warmed to 60° C. for one hour. The reaction mixed was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was recrystallized from methylene chloride and hexane to give product (0.25 g, 0.7 mol, 36 percent) yield.

Workup

  1. additionThe reaction mixed
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from methylene chloride and hexane

Sources & evidence

ORD record
ord-5502818518c34b02af5acf3326f44e92
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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