Tetrahydrofuran → 5-bromo-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine

HRID 1042741

Reaction equation

[Br:1][C:2]1[C:3]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.C1COCC1.[CH2:19]([N:21](CC)CC)C.Cl.CN>O>[Br:1][C:2]1[C:3]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:4][C:5]([NH:21][CH3:19])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A 16 by 100 mm vial was charged with 5-bromo-2-chloro-4-(thiophen-2-yl)pyrimidine (1.00 g, 3.6 mmol), THF (4 mL), triethylamine (1.5 ml, 11 mmol), and methylamine hydrochloride (0.49 g, 7.3 mmol), and water (0.4 mL). The vial was capped and heated to 85° C. with stirring for 20 hours. The reaction was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0 to 4% methanol in dichloromethane) to afford 5-bromo-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine. MS m/z=271 [M+H]+. Calc'd for C9H8BrN3S: 270.

Workup

customThe vial was capped
temperatureThe reaction was cooled to room temperature
concentrationconcentrated
customThe residue was purified via column chromatography on silica gel (gradient elution with 0 to 4% methanol in dichloromethane)

Sources & evidence

ORD record: ord-a4ca13539fe8491ea663103627391492
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557996B2

Linked notes

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