Triethylamine → HCID 57971149, compound

HRID 602305Notes

Reaction equation

HRID 602305 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8]OS(C)(=O)=O)[CH:5]=[CH:4][N:3]=1.[SH:14][C:15]1[N:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][S:14][C:15]2[N:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 579711404-Pyrimidinemethanol, 2-amino-, 4-methanesulfonateHCID 178524460HCID 178524460, compound

Product 1

HCID 57971149HCID 57971149, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-methanesulfonyloxymethylpyrimidine (580 mg, 2.9 mmol, Reference Compound No. 8-1) was suspended in N,N-dimethylformamide (15 mL), and 2-mercaptonicotinic acid (400 mg, 2.6 mmol) and triethylamine (1.2 mL, 8.6 mmol) were added thereto under ice-cooling, and the mixture was stirred for 21 hours at room temperature. The reaction mixture was diluted with ethyl acetate (50 mL), and extracted with water (50 mL) and saturated aqueous sodium hydrogencarbonate solution (30 mL). 2M hydrochloric acid was added to the aqueous layer until bubbles were no longer formed, and the precipitated solid was filtered off. The solid was dried at 55° C. under reduced pressure, to give 470 mg of the title Reference Compound as a white solid (Yield: 70%).

Workup

  1. temperatureunder ice-cooling
  2. extractionextracted with water (50 mL) and saturated aqueous sodium hydrogencarbonate solution (30 mL)
  3. addition2M hydrochloric acid was added to the aqueous layer until bubbles
  4. customwere no longer formed
  5. filtrationthe precipitated solid was filtered off
  6. customThe solid was dried at 55° C. under reduced pressure

Sources & evidence

ORD record
ord-169ce0881e364805bf4c36ab72a6701f
Source dataset
uspto-grants-2011_03
Patent number
US07906511B2

Reaction notes

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