Guanidine Hydrochloride → 2-methyl-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-8-amine

HRID 2102797Notes

Reaction equation

HRID 2102797 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:10](=O)[C:9](=[CH:12]N3CCOCC3)[CH2:8][CH2:7][C:5]=2[N:6]=1.Cl.[NH2:20][C:21]([NH2:23])=[NH:22].[OH-].[Na+]>CCO>[CH3:1][C:2]1[S:3][C:4]2[C:10]3[N:20]=[C:21]([NH2:23])[N:22]=[CH:12][C:9]=3[CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 684158522-Methyl-6-morpholin-4-ylmethylene-5,6-dihydro-4H-benzothiazol-7-one

Product 1

HCID 112874152-methyl-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-8-amineYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-6-morpholin-4-ylmethylene-5,6-dihydro-4H-benzothiazol-7-one (2.24 g, 8.47 mol), guanidine hydrochloride salt (0.89 g, 9.32 mol) and NaOH (0.37 g, 9.32 mol) in EtOH (150 mL) was heated under reflux for 4 h. The reaction mixture was concentrated under vacuum. Flash column chromatography (50% EtOAc:hexane) afforded the title product as a yellow solid (1.66 g, 90%): mp 241-243° C. Anal. RP-HPLC: tR 8.7 min (0-60% MeCN, purity 100%). 1H-NMR (CDCl3): δ 8.06 (s, 1H, Py-H), 5.01 (brs, 2H, NH2), 2.99 (m, 4H, CH2—CH2), 2.76 (s, 3H, CH3). MS (ESI+): m/z 219.02 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-d5f8e40a6cee48629c3ec7d86feb55fc
Source dataset
uspto-grants-2009_08
Patent number
US07576091B2

Reaction notes

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