Sodium hydride → (1-Ethyl-propyl)-[2-methyl-nitro-6-(2,4,6-trimethyl-pyridin-3-yloxy)-pyrimidin-4-yl]-amine

HRID 1245694Notes

Reaction equation

HRID 1245694 reaction equation
[OH:1][C:2]1[C:3]([CH3:10])=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8].[H-].[Na+].Cl[C:14]1[N:19]=[C:18]([CH3:20])[N:17]=[C:16]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:15]=1[N+:27]([O-:29])=[O:28]>C1COCC1>[CH2:23]([CH:22]([NH:21][C:16]1[C:15]([N+:27]([O-:29])=[O:28])=[C:14]([O:1][C:2]2[C:3]([CH3:10])=[N:4][C:5]([CH3:9])=[CH:6][C:7]=2[CH3:8])[N:19]=[C:18]([CH3:20])[N:17]=1)[CH2:25][CH3:26])[CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1476252,4,6-Trimethyl-3-hydroxypyridineHCID 159085846-Chloro-2-methyl-5-nitro-N-(pentan-3-yl)pyrimidin-4-amine

Product 1

HCID 21912377(1-Ethyl-propyl)-[2-methyl-nitro-6-(2,4,6-trimethyl-pyridin-3-yloxy)-pyrimidin-4-yl]-amineYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 3-hydroxy-2,4,6-trimethylpyridine (41 mg, 0.3 mmol) in 1 ml of dry THF was treated with 60% sodium hydride in oil (13 mg, 0.3 mmol) at rt. The reaction mixture was cooled to −78° C. and a solution of (6-chloro-2-methyl-5-nitro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (78 mg, 0.3 mmol) in 1 ml of dry THF was added. The reaction was stirred at −78° C. for 1 hour, quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 91 mg (84%) of white solid of the title compound, mp 134–135° C. 1H NMR (CDCl3) δ 8.30 (d, 1H), 6.89 (s, 2H), 4.30 (m, 1H), 2.31 (s, 3H), 2.26 (s, 3H), 2.10 (s, 6H), 1.5–1.8 (m, 4H), 0.97 (t, 6H) ppm.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-db083880c1184b0498228eea3ffa7912
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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