Hydrochloric Acid → HCID 178433428, compound

HRID 1958013Notes

Reaction equation

HRID 1958013 reaction equation
[C:1](OC(=O)C)(=O)[CH3:2].[NH2:8][C:9]1[N:10]=[C:11]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[S:12][C:13]=1[C:14]([NH2:16])=[O:15].[OH-].[Na+].Cl>C(O)C.C(O)(=O)C>[CH3:1][C:2]1[NH:8][C:9]2[N:10]=[C:11]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[S:12][C:13]=2[C:14](=[O:15])[N:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 13595332HCID 13595332, compound

Product 1

HCID 178433428HCID 178433428, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of acetic anhydride (4 ml, 42.4 mmol), Acetic Acid (2.00 ml) and 4-amino-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (200 mg, 0.876 mmol) was stirred at 60° C. for 3 h, then quenched with methanol and concentrated under reduced pressure. A mixture of the residue, Ethanol (2.000 ml) and 6N NaOH (2 ml, 12.00 mmol) was irradiated (uwave) at 120° C. for 30 min, then acidified with 6N HCl to pH ˜5. The precipitate was collected, rinsed with water, and dried under vacuum to furnish 5-methyl-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (175 mg, 79%). LC/MS: MS(ES+) m/e 253 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.31 (s, 3H) 3.54-3.59 (m, 4H) 3.69-3.75 (m, 4H) 12.34 (br. s., 1H).

Workup

  1. customquenched with methanol
  2. concentrationconcentrated under reduced pressure
  3. customwas irradiated (uwave) at 120° C. for 30 min
  4. customThe precipitate was collected
  5. washrinsed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-392c74d283004a988e5e5f0c56c2ad8e
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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