Tetrahydrofuran → 2-[(2-Guanidinoethyl)amino]-4-(3-methylanilino)pyrimidine-5-carboxamide nitrate

HRID 2303310Notes

Reaction equation

[N+:1]([O-:4])([OH:3])=[O:2].CC1C=C(C)[N:8]([C:12](N)=[NH:13])N=1.C(N(C(C)C)CC)(C)C.[NH2:24][CH2:25][CH2:26][NH:27][C:28]1[N:33]=[C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[CH:36]=2)[C:31]([C:42]([NH2:44])=[O:43])=[CH:30][N:29]=1.C1COCC1>C(OCC)(=O)C.O>[N+:1]([O-:4])([OH:3])=[O:2].[NH:24]([CH2:25][CH2:26][NH:27][C:28]1[N:33]=[C:32]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[CH:36]=2)[C:31]([C:42]([NH2:44])=[O:43])=[CH:30][N:29]=1)[C:12]([NH2:13])=[NH:8]

Participants

Conditions

Temperature: 60 °C

Procedure

A 508 mg portion of 3,5-dimethylpyrazole-1-carboxamidine nitrate and 876 μl of diisopropylethylamine were added to a mixture of 328 mg of 2-(2-aminoethylamino)-4-(3-methylanilino)pyrimidine-5-carboxamide and THF, followed by stirring at 60° C. for one week. Water and ethyl acetate were added to the reaction mixture, and the water layer was concentrated under a reduced pressure. The resulting residue was washed with a mixed solution of methanol and ethyl acetate and then recrystallized from a mixed solvent of methanol and water to obtain 200 mg of 2-[(2-guanidinoethyl)amino]-4-(3-methylanilino)pyrimidine-5-carboxamide nitrate as colorless crystals.

Workup

concentrationthe water layer was concentrated under a reduced pressure
washThe resulting residue was washed with a mixed solution of methanol and ethyl acetate
customrecrystallized from a mixed solvent of methanol and water

Sources & evidence

ORD record: ord-5f7a9913ccaf4be495b6b77a60ca4afc
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06432963B1

Reaction notes

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