Toluene → HCID 21912433, compound

HRID 1245699Notes

Reaction equation

HRID 1245699 reaction equation
[CH2:1]([N:5]([CH2:24][CH3:25])[C:6]1[C:11]([NH:12][C:13]2[C:18](C)=CC(C)=CC=2C)=[C:10]([NH2:22])[N:9]=[C:8]([CH3:23])[N:7]=1)[CH2:2][CH2:3][CH3:4].C(O[CH2:35][CH3:36])(OCC)(OCC)C.[CH3:37][C:38]1[CH:39]=C[C:41](S(O)(=O)=O)=[CH:42][CH:43]=1.[C:48]1(C)C=CC=CC=1>>[CH2:1]([N:5]([C:6]1[N:7]=[C:8]([CH3:23])[N:9]=[C:10]2[C:11]=1[N:12]=[C:13]([CH3:18])[N:22]2[C:48]1[C:42]([CH3:41])=[CH:43][C:38]([CH3:37])=[CH:39][C:35]=1[CH3:36])[CH2:24][CH3:25])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 66221Triethyl orthoacetateHCID 21912300HCID 21912300, compound

Product 1

HCID 21912433HCID 21912433, compound

Procedure

A mixture of N-butyl-N-ethyl-2-methyl-N′-(2,4,6-trimethylphenyl)-pyrimidine-4, 5,6-triamine (105 mg, 0.63 mmol) and triethyl orthoacetate (0.204 g, 1.25 mmol) and 10 mg of p-TsOH in toluene was heated reflux overnight. The mixture was concentrated to dryness and the residue was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give yellow oil. The oil was purified through silica gel column chromatography using 1:1 of hexane:chloroform as eluent to give the title compound. 1H NMR(CDCl3) δ 7.01(s,2H), 3.9–4.1(m,4H), 2.45(s,3H), 2.35(s,3H), 2.20(s,3H), 1.91(s,6H), 1.6–1.8(m,2H), 1.35–1.5(m,2H), 1.29(t,3H), 0.99(t,3H) ppm.

Workup

  1. temperaturewas heated
  2. temperaturereflux overnight
  3. concentrationThe mixture was concentrated to dryness
  4. customthe residue was quenched with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customto give yellow oil
  9. customThe oil was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-88e24bffdc9b48eab14896c39049cd20
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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