HCID 55091508, compound → HCID 178426363, compound

HRID 2061441Notes

Reaction equation

HRID 2061441 reaction equation
[CH2:1]([N:8]([CH3:17])[C:9]1[CH:10]=[C:11]([NH2:16])[CH:12]=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21](SC)[N:20]=1>CO>[CH2:1]([N:8]([CH3:17])[C:9]1[CH:10]=[C:11]([NH:16][C:21]2[N:20]=[C:19]([OH:18])[CH:24]=[CH:23][N:22]=2)[CH:12]=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 55091508HCID 55091508, compoundHCID 178503462HCID 178503462, compound

Product 1

HCID 178426363HCID 178426363, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

An intimate mixture of N3-benzyl-N3,4-dimethyl-benzene-1,3-diamine (158 mg, 0.7 mmol) and 4-hydroxy-2-methylthio-pyrimidine (109 mg, 0.77 mmol) is heated in an oil bath of 160° C. After 3 h the melt is cooled to room temperature and treated with MeOH. The remaining solid is collected by filtration, washed with MeOH, and dried, giving 65.5 mg (29%) of N3-benzyl-N1-(4-hydroxy-pyrimidin-2-yl)-N3,4-dimethyl-benzene-1,3-diamine.

Workup

  1. temperatureAfter 3 h the melt is cooled to room temperature
  2. filtrationThe remaining solid is collected by filtration
  3. washwashed with MeOH
  4. customdried

Sources & evidence

ORD record
ord-0b4cf835f9004e529d2e91b3d18163f8
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

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