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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1962250Generated: 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/1962250

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 numberUS08415365B2
Source datasetuspto-grants-2013_04
ORD IDord-4b0bd3f58a4a4c97b4029a93eb7e6cd1
Source noteuspto-grants-2013_04