Lithium Hydroxide → 4-(3-iodo-1-(1-methylethyl)-1H-pyrazol-4-yl)-2-pyrimidinamine

HRID 1889237Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:8]([I:15])=[N:9][N:10]([CH:12]([CH3:14])[CH3:13])[CH:11]=1)=O.Cl.[NH2:18][C:19]([NH2:21])=[NH:20].[OH-].[Li+]>C(O)(CC)C>[I:15][C:8]1[C:7]([C:5]2[CH:4]=[CH:3][N:18]=[C:19]([NH2:21])[N:20]=2)=[CH:11][N:10]([CH:12]([CH3:14])[CH3:13])[N:9]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of crude Intermediate 3-(dimethylamino)-1-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)prop-2-en-1-one (4.0 g, 12.0 mmol), guanidine hydrochloride (2.63 g, 27.6 mmol), lithium hydroxide (635 mg, 27.6 mmol), and sec-butanol (50 ml) was heated with stirring in a sealed reaction vessel at 110° C. for 20 h. The cooled reaction mixture was concentrated, then water was added and the mixture was extracted with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered, and concentrated. Ethyl acetate was added to the solid residue, and the mixture was sonicated. The solid product was collected on a filter, rinsed with ethyl acetate, and dried to give the title compound as a tan solid. MS m/z 330.0 (M+1).

Workup

temperaturewas heated
customThe cooled reaction mixture
concentrationwas concentrated
additionwater was added
extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
additionEthyl acetate was added to the solid residue
customthe mixture was sonicated
customThe solid product was collected on a filter
washrinsed with ethyl acetate
customdried

Sources & evidence

ORD record: ord-0eb4e016395f4ec59ed547e46e1e8a06
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501758B2

Reaction notes

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