Tetrahydrofuran → N-(1-Ethyl-propyl)-2-methyl-5-nitro-N'-(2,4,6-trimethyl-pyridin-3-yl)-pyrimidine-4,6-diamine

HRID 1760671

Reaction equation

HRID 1760671 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[C:11]([CH3:18])=[N:12][C:13]([CH3:17])=[CH:14][C:15]=2[CH3:16])[C:3]=1[N+:19]([O-:21])=[O:20].C([NH:24][CH2:25][CH2:26][CH3:27])C.[CH2:28]1COC[CH2:29]1>>[CH2:28]([CH:25]([NH:24][C:2]1[C:3]([N+:19]([O-:21])=[O:20])=[C:4]([NH:9][C:10]2[C:11]([CH3:18])=[N:12][C:13]([CH3:17])=[CH:14][C:15]=2[CH3:16])[N:5]=[C:6]([CH3:8])[N:7]=1)[CH2:26][CH3:27])[CH3:29]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 883981-Propanamine, N-ethyl-HCID 10757155(6-Chloro-2-methyl-5-nitro-pyrimidin-4-yl)(2,4,6-trimethyl-pyridin-3-yl)amine

Product 1

HCID 9820165N-(1-Ethyl-propyl)-2-methyl-5-nitro-N'-(2,4,6-trimethyl-pyridin-3-yl)-pyrimidine-4,6-diamineYield 86%

Conditions

Temperature
-10 °C

Procedure

To a cooled solution of (6-chloro-2-methyl-5-nitro-pyrimidin-4-yl(2,4,6-trimethyl-pyridin-3-yl)-amine (88 mg, 0.29 mmol) in 1 ml of dry THF was added 1 ethyl-propyl-amine (80 mg, 0.92 mmol) at −78° C. The mixture was stirred at that temperature for 3 hrs, then warmed to −10° C. for 1 hour. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give the title compound (88 mg, 86%) as an orange solid, mp 151-152° C. 1H NMR (CDCl3) δ 9.16 (d, 1H), 6.92 (s, 1H), 4.35 (m, 1H), 2.50 (s, 3H), 2.39 (s, 3H), 2.18 (s, 3H), 2.16 (s, 3H), 1.5-1.80 (m, 4H), 0.94 (t, 6H) ppm.

Workup

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

Sources & evidence

ORD record
ord-bae5b9f85ab34f1189c94b13e1c6b5c9
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Linked notes

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