Hydrochloric Acid → HCID 59286679, compound

HRID 1876024Notes

Reaction equation

HRID 1876024 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11]C(=O)OCC)=[N:10][C:5]2=[N:4][CH:3]=1.[OH-].[Na+].Cl>>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([NH2:11])=[N:10][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59286703HCID 59286703, compound

Product 1

HCID 59286679HCID 59286679, compoundYield 50.6%

Conditions

Temperature
100 °C

Procedure

Ethyl 6-methylthiazolo[5,4-b]pyrazin-2-ylcarbamate (660 mg, 2.77 mmol) was suspended in 1N NaOH (15 ml, 15.00 mmol) and heated in a 100° C. oil bath for 4 h and cooled to ambient temperature. The mixture was acidified with 1N HCl and the resulting precipitate was filtered off and washed with ether, affording 6-methylthiazolo[5,4-b]pyrazin-2-amine (233 mg, 1.402 mmol, 50.6% yield) as a yellow powder. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.26 (s, 2H) 8.12 (s, 1H) 2.43 (s, 3H). MS (LC/MS) R.T.=0.66; [M+H]+=167.0.

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationthe resulting precipitate was filtered off
  3. washwashed with ether

Sources & evidence

ORD record
ord-588f5a705fc742a1aa133458ab65fde5
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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