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

HRID 1962250Notes

Reaction equation

HRID 1962250 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[CH:13]=1.[Cl:14][C:15]1[N:20]=[C:19](Cl)[C:18]([CH3:22])=[CH:17][N:16]=1>CO>[Cl:14][C:15]1[N:20]=[C:19]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[S:10][CH2:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=3[CH:13]=2)[C:18]([CH3:22])=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 219881476-Amino-4-methyl-2H-1,4-benzothiazin-3(4H)-one

Product 1

HCID 866097232-Chloro-5-methyl-N4-(4-methyl-3-oxo-benzo[1,4]thiazin-6-yl)-4-pyrimidineamineYield 30.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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+).

Workup

  1. customwas reduced in volume by rotary evaporation
  2. filtrationThe solution was filtered
  3. additionthe filtrate diluted with water and neutralized with sodium bicarbonate
  4. filtrationThe precipitate was collected by suction filtration
  5. washwashed with water
  6. customdried on the funnel

Sources & evidence

ORD record
ord-4b0bd3f58a4a4c97b4029a93eb7e6cd1
Source dataset
uspto-grants-2013_04
Patent number
US08415365B2

Reaction notes

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