2,4,5-Trichloropyrimidine → 2,5-Dichloro-4-methylpyrimidine

2,4,5-trichloropyrimidine (1.83 g, 10 mmol) was dissolved in THF:NMP (10:1, 100 mL) at room temperature and iron(III) acetylacetonate (0.71 g, 2.0 mmol) was added under N2. MgBrMe (3M, 12 mmol) was added drop-wise via syringe. The mixture was cooled to RT, progress was verified by LC-MS: typical results show product vs starting material vs 5-chloro-2,4-dimethylpyrimidine side product ˜2:2:1 ratio. The reaction was quenched with ice cold, saturated ammonium chloride (, 100 mL), extracted with ethyl acetate (100 mL), washed with brine (100 mL, ×2), dried over MgSO4, filtered and concentrated i. vac. The crude mixture was purified by silica gel chromatography (5% ethylacetate/hexane) to yield the titled compound.

1. additionMgBrMe (3M, 12 mmol) was added drop-wise via syringe
2. customtypical results
3. customThe reaction was quenched with ice cold, saturated ammonium chloride (, 100 mL)
4. extractionextracted with ethyl acetate (100 mL)
5. washwashed with brine (100 mL, ×2)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated i
9. customThe crude mixture was purified by silica gel chromatography (5% ethylacetate/hexane)

ORD record

ord-943240b68aad4ceebe206f50d9d2e988

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343990B2