Methanol → Methyl 2-(2-(1H-tetrazol-1-yl)pyrimidin-5-yl)acetate

HRID 1502153Notes

Reaction equation

HRID 1502153 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][N:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.S(=O)(=O)(O)O.[CH3:21]O>>[N:1]1([C:6]2[N:7]=[CH:8][C:9]([CH2:12][C:13]([O:15][CH3:21])=[O:14])=[CH:10][N:11]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 89619099[2-(1H-tetrazol-1-yl)pyrimidin-5-yl]acetic acid

Product 1

HCID 89619075Methyl 2-(2-(1H-tetrazol-1-yl)pyrimidin-5-yl)acetate

Procedure

To a solution of 2-(2-(1H-tetrazol-1-yl)pyrimidin-5-yl)acetic acid (100 mg, 0.485 mmol) in methanol (30 mL) was added sulfuric acid (1 mL, 18.8 mmol). Stirred at room temperature and sonicated to dissolve all acid starting material. Reaction was complete within about 2-3 min. The reaction was concentrated under reduced pressure, neutralized with saturated aqueous sodium bicarbonate, extracted with DCM (2 times), washed organics with brine, dried over magnesium sulfate. Solvent was removed under reduced pressure and residue dried on high vacuum overnight. LC/MS: [(M+1)]+=221.0;

Workup

  1. customsonicated
  2. dissolutionto dissolve all acid
  3. customReaction
  4. concentrationThe reaction was concentrated under reduced pressure
  5. extractionextracted with DCM (2 times)
  6. washwashed organics with brine
  7. dry with materialdried over magnesium sulfate
  8. customSolvent was removed under reduced pressure and residue
  9. customdried on high vacuum overnight

Sources & evidence

ORD record
ord-1763c275fe3b4009981330202e4cf02e
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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