Sodium Hydroxide → HCID 486392, compound

HRID 1363890Notes

Reaction equation

HRID 1363890 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1.[NH2:18][C:19]1[C:26]([CH3:27])=[CH:25][C:22]([C:23]#[N:24])=[CH:21][C:20]=1[CH3:28].C(N(C(C)C)CC)(C)C.[OH-].[Na+]>C(Cl)Cl.O1CCOCC1.CN1CCCC1=O>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([NH:9][C:4]2[N:3]=[C:2]([NH:18][C:19]3[C:20]([CH3:28])=[CH:21][C:22]([C:23]#[N:24])=[CH:25][C:26]=3[CH3:27])[C:7]([CH3:8])=[CH:6][N:5]=2)=[CH:11][CH:12]=1)#[N:15]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2789444-amino-3,5-dimethylbenzonitrileHCID 86583607HCID 86583607, compound

Product 1

HCID 486392HCID 486392, compoundYield 202.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
195 °C

Procedure

4-[[4-[(4-chloro-5-methyl-2-pyrimidinyl]amino]benzonitrile (0.01541 mol), 4-amino-3,5-dimethyl-benzonitrile (0.00219 mol), 1-methyl-2-pyrrolidinone (4 ml), 1,4-dioxane (15 ml) and diisopropylethylamine (0.0154 mol) were combined in a flask under a stream of argon and heated at 160-230° C. for 16 hours. CH2Cl2 and 1N NaOH were added, and the mixture was stirred 1 hour and filtered to give a brown solid (!). The CH2Cl2 filtrate was separated and was evaporated and purified by flash column chromatography (eluent: 2% CH3OH/CH2Cl2). The desired fractions were combined, evaporated and the residue was stirred in CH2Cl2. The solid precipitate was filtered off, combined with the brown solid (!) and recrystallized from CH3CN. The precipitate was filtered off and dried, yielding 1.57 g (29%) of 4-[[2-[(4-cyanophenyl)amino]-5-methyl-4-pyrimidinyl]amino]-3,5-dimethylbenzonitrile (comp. 52).

Workup

  1. filtrationfiltered
  2. customto give a brown solid (!)
  3. customThe CH2Cl2 filtrate was separated
  4. customwas evaporated
  5. custompurified by flash column chromatography (eluent: 2% CH3OH/CH2Cl2)
  6. customevaporated
  7. stirringthe residue was stirred in CH2Cl2
  8. filtrationThe solid precipitate was filtered off
  9. customrecrystallized from CH3CN
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-a5a67f10f5fa421c9cd9909b134bc90a
Source dataset
uspto-grants-2011_02
Patent number
US07887845B2

Reaction notes

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