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

HRID 1947602Notes

Reaction equation

HRID 1947602 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-03c5d93064fa4b538cfebf502e5879d4
Source dataset
uspto-grants-2013_03
Patent number
US08399472B2

Reaction notes

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