4-Amino-2-chloropyrimidine-5-carbonitrile → HCID 22393271, compound

HRID 1071351Notes

Reaction equation

HRID 1071351 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4](Cl)[N:3]=1.[N:11]1([CH2:16][CH2:17][CH2:18][NH:19][C:20]([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)=[O:21])[CH:15]=[CH:14][N:13]=[CH:12]1>CN1C(=O)CCC1.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([NH:26][C:25]2[CH:27]=[CH:28][C:22]([C:20](=[O:21])[NH:19][CH2:18][CH2:17][CH2:16][N:11]3[CH:15]=[CH:14][N:13]=[CH:12]3)=[CH:23][CH:24]=2)[N:3]=1

Participants

5

Reactant 2

HCID 28011664-Amino-2-chloropyrimidine-5-carbonitrileHCID 22393276HCID 22393276, compound

Product 1

HCID 22393271HCID 22393271, compoundYield 2.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-amino-2-chloro-5-cyanopyrimidine (200 mg, 1.3 mmol) and 4-[N-(3-imidazol-1-ylpropyl)carbamoyl]aniline (Method 3; 633 mg, 2.6 mmol) in NMP (10 ml) was heated at 120° C. for 48 hours. The mixture was allowed to cool, was diluted with water and extracted with ethyl acetate. The organic extracts were combined, dried and the solvent removed by evaporation, the residue was triturated with ether/hexane and the product collected by filtration to give the title compound (10 mg, 2%). NMR: 1.92 (q, 2H) 3.20 (q, 2H), 4.00 (t, 2H), 6.87 (s, 1H), 7.19 (s, 1H), 7.55 (s, 2H), 7.62 (s, 1H), 7.86 (d, 2H), 8.32 (t, 1H), 8.38 (s,1H), 9.90 (s, 1H); m/z 363 (MH)+.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. customdried
  4. customthe solvent removed by evaporation
  5. customthe residue was triturated with ether/hexane
  6. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-fd3ffb2d14a544d8ae734a2117d1815b
Source dataset
uspto-grants-2005_06
Patent number
US06906065B2

Reaction notes

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