HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyrimidine, 2,4-dichloro-5-methyl- → 2-Chloro-5-methyl-N4-(4-methyl-3-oxo-benzo[1,4]thiazin-6-yl)-4-pyrimidineamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyrimidine, 2,4-dichloro-5-methyl- | HCID 74508 | — |
| Reactant | 6-Amino-4-methyl-2H-1,4-benzothiazin-3(4H)-one | HCID 21988147 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 2-Chloro-5-methyl-N4-(4-methyl-3-oxo-benzo[1,4]thiazin-6-yl)-4-pyrimidineamine | HCID 86609723 | 30.7% |
Reaction Steps
A mixture of 1.3 g of 6-Amino-4-methyl-3-oxo-benzo[1,4]thiazine and 3.3 g of 2,4-Dichloro-5-methylpyrimidine in 100 mL methanol was stirred at RT overnight and was reduced in volume by rotary evaporation. The solution was filtered and the filtrate diluted with water and neutralized with sodium bicarbonate. The precipitate was collected by suction filtration washed with water and dried on the funnel to yield 660 mg 13% of the desired product 2-Chloro-5-methyl-N4-(4-methyl-3-oxo-benzo[1,4]thiazin-6-yl)-4-pyrimidineamine 1H NMR (DMSO-d6): δ 8.93 (s, 1H), 8.06 (m, 2H), 7.62 (s, 1H), 7.37 (s, 1H), 3.51 (s, 2H), 2.16 (s, 3H) purity 97%; MS (m/e) 321 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415365B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-4b0bd3f58a4a4c97b4029a93eb7e6cd1 |
| Source note | uspto-grants-2013_04 |