Hydrochloric Acid → (6-Aminopyrimidin-4-yl)methanol

HRID 2366182Notes

Reaction equation

HRID 2366182 reaction equation
Cl.C(OC(=O)[NH:8][C:9]1[CH:14]=[C:13]([CH2:15][OH:16])[N:12]=[CH:11][N:10]=1)(C)(C)C>CO>[NH2:8][C:9]1[N:10]=[CH:11][N:12]=[C:13]([CH2:15][OH:16])[CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 72698493tert-Butyl (6-(hydroxymethyl)pyrimidin-4-yl)carbamate

Product 1

HCID 21934615(6-Aminopyrimidin-4-yl)methanolYield 181.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Concentrated hydrochloric acid (0.80 mL) was added to a solution of tert-butyl-6-(hydroxymethyl)pyrimidin-4-ylcarbamate (0.50 g, 2.2 mmol) in MeOH (10 mL). The reaction was stirred at 25° C. for 1 hour and then concentrated under reduced pressure to give the desired compound (0.50 g) as a pale yellow solid, which was used in the next step without further purification. LCMS (ESI) m/z: 126.0 [M+H+].

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ee2171d8ce14c84bfb1b34a2b61bd25
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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