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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1770846Generated: 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/1770846

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 numberUS09248190B2
Source datasetuspto-grants-2016_02
ORD IDord-5be4699250834d1e924219ed630d810d
Source noteuspto-grants-2016_02