Guanidine Hydrochloride → 4-(1,1-Dimethoxyethyl)pyrimidin-2-amine

HRID 969698Notes

Reaction equation

Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[O-]CC.[Na+].CN(C)[CH:12]=[CH:13][C:14](=O)[C:15]([O:19][CH3:20])([O:17][CH3:18])[CH3:16]>CCO>[CH3:18][O:17][C:15]([C:14]1[CH:13]=[CH:12][N:2]=[C:3]([NH2:5])[N:4]=1)([O:19][CH3:20])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

To guanidine hydrochloride salt (15 g, 156.68 mmol) was added sodium ethoxide, 21% wt in EtOH (59 mL, 156.68 mmol). After stirring for 5 min, 1-dimethylamino-4,4-dimethoxy-pent-1-en-3-one (Lipinski; J. Het. Chem., 22:1723 (1995)) (29.30 g, 156.68 mmol) in EtOH (50 mL) was added. The mixture was heated at 80° C. under N2 for 20 h, then cooled to RT. Solvent was evaporated in vacuo and the residue was re-dissolved in hot EtOAc (200 mL). The undissolved solid was separated by filtration and the solvent was evaporated in vacuo to give a pale yellow solid. MS m/z:184.3(M+H). Calc'd for C8H14N3O2: 184.21.

Workup

temperaturecooled to RT
customSolvent was evaporated in vacuo
dissolutionthe residue was re-dissolved in hot EtOAc (200 mL)
customThe undissolved solid was separated by filtration
customthe solvent was evaporated in vacuo
customto give a pale yellow solid

Sources & evidence

ORD record: ord-02a5834a106e41c4a03d72fa32e10d5c
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07307088B2

Reaction notes

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