Trifluoroacetic acid → [2-(1H-tetrazol-1-yl)pyrimidin-5-yl]acetic acid

HRID 1502149Notes

Reaction equation

HRID 1502149 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:26])[CH2:14][C:15]1[CH:16]=[N:17][C:18]([N:21]2[CH:25]=[N:24][N:23]=[N:22]2)=[N:19][CH:20]=1)(C)(C)C>ClCCl>[N:21]1([C:18]2[N:17]=[CH:16][C:15]([CH2:14][C:13]([OH:26])=[O:12])=[CH:20][N:19]=2)[CH:25]=[N:24][N:23]=[N:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131734297tert-butyl[2-(1H-tetrazol-1-yl)pyrimidin-5-yl]acetate

Product 1

HCID 89619099[2-(1H-tetrazol-1-yl)pyrimidin-5-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (36 mL, 467 mmol) was added slowly to a solution of tert-butyl[2-(1H-tetrazol-1-yl)pyrimidin-5-yl]acetate (9.80 g, 37.4 mmol) in dichloromethane (36 mL) at RT. The reaction mixture was stirred at RT overnight then evaporated. The residue was triturated with ether:hexane (1:1) (100 mL). The solid was triturated with acetonitrile to afford title compound: 1H NMR 600 MHz (CD3OD) 10.01 (s, 1H); 8.94 (s, 2H); 3.88 (s, 2H); LC/MS (M+Na)+ at 229, (M+1)+ at 207, and (M+1-N2)+ at 179.

Workup

  1. customthen evaporated
  2. customThe residue was triturated with ether:hexane (1:1) (100 mL)
  3. customThe solid was triturated with acetonitrile

Sources & evidence

ORD record
ord-ad280758cd2e49aaabd755f7f62a7569
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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