Dimethylformamide → HCID 67456046, compound

HRID 2093291Notes

Reaction equation

HRID 2093291 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.N[CH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].C[N:27](C)C=O>>[NH2:1][CH:2]1[N:7]=[C:6]([CH:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)[CH:5]=[C:4]([CH3:9])[N:3]1[NH2:27]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 123445(+-)-1-Aminoindan

Product 1

HCID 67456046HCID 67456046, compound

Conditions

Temperature
145 °C

Procedure

A mixture of 2.9 g (20 mmol) of 2-amino-4-chloro-6-methylpyrimidine, 2.9 g (22 mmol) of 1-aminoindane and 4.1 g (30 mmol) of potassium carbonate in 30 ml of dimethylformamide is heated at 145° C. for 3 hours. After cooling, the reaction mixture is hydrolyzed, the aqueous mixture is extracted with methylene chloride, the separated-off organic phase is dried with sodium sulfate. After filtering off the drying agent and concentrating the organic phase by evaporation, the crude mixture is separated by means of column chromatographic separation using ethyl acetate/methanol/triethylamine 90/10/1 as eluent. The 2-amino-4-indanyl-1-amino-6-methylpyrimidine obtained in this way is taken up in ethyl acetate/heptane 2:8 and treated with activated carbon. After separating off the activated carbon and concentrating the solvent by evaporation, 1 g of 2-amino-4-indanyl-1-amino-6-methylpyrimidine is obtained (glass-like solid, m.p: 53-54° C., 20% yield, 95% purity).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous mixture is extracted with methylene chloride
  3. dry with materialthe separated-off organic phase is dried with sodium sulfate
  4. filtrationAfter filtering off the drying agent
  5. concentrationconcentrating the organic phase
  6. customby evaporation
  7. customthe crude mixture is separated by means of column chromatographic separation

Sources & evidence

ORD record
ord-dee9d0b676bb4e53bb4ca8c4f552e8f5
Source dataset
uspto-grants-2013_05
Patent number
US08445408B2

Reaction notes

Loading…