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

HRID 502785Notes

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-a2f2312c23c944e89b950f79692acdec
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776869B2

Reaction notes

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