Hydrochloric Acid → HCID 178477359, compound

HRID 1637734Notes

Reaction equation

HRID 1637734 reaction equation
[Si]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si](C(C)(C)C)(C)C)[N:12]=[C:11]([S:23][CH:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH3:25])[N:10]=1)(C(C)(C)C)(C)C.[ClH:32]>O1CCCC1>[ClH:32].[OH:15][C:13]1[CH:14]=[C:9]([OH:8])[N:10]=[C:11]([S:23][CH:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH3:25])[N:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18799741HCID 18799741, compound

Product 1

HCID 178477359HCID 178477359, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,6-di-(tert-butyldimethylsilyloxy)-2-(1-(2-pyridyl)ethyl)thio-pyrimidine (1.23 g, 2.58 mmol) in 8 ml of tetrahydrofuran is treated with 2 N HCl (5.2 ml, 10.31 mmol, 4.0 equiv.) at room temperature. After 30 min, the reaction mixture is concentrated directly at reduced pressure, diluted with toluene and reconcentrated again. The resulting white solid is triturated with methylene chloride, collected and dried to obtain 0.819 g of crude 4,6-dihydroxy-2-(1-(2-pyridyl)ethyl)thio-pyrimidine hydrochloride.

Workup

  1. concentrationthe reaction mixture is concentrated directly at reduced pressure
  2. additiondiluted with toluene
  3. customThe resulting white solid is triturated with methylene chloride
  4. customcollected
  5. customdried

Sources & evidence

ORD record
ord-b8890807299a4a46aba7c7256352b6b8
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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