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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2408396Generated: October 25, 2026

Pyrimidine, 2,4-dichloro-5-methyl- → 2-Chloro-5-methyl-N4-(4-methyl-3-oxo-benzo[1,4]thiazin-6-yl)-4-pyrimidineamine

https://huagongshe.com/reaction/2408396

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyrimidine, 2,4-dichloro-5-methyl-HCID 74508—
Reactant6-Amino-4-methyl-2H-1,4-benzothiazin-3(4H)-oneHCID 21988147—
SolventMethanolHCID 887—
Product2-Chloro-5-methyl-N4-(4-methyl-3-oxo-benzo[1,4]thiazin-6-yl)-4-pyrimidineamineHCID 8660972330.7%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08815848B2
Source datasetuspto-grants-2014_08
ORD IDord-bd966cee18a4482897e923b38a6b4151
Source noteuspto-grants-2014_08