2,4-Dichloro-6-methylpyrimidine → HCID 86618732, compound

HRID 1397607Notes

Reaction equation

HRID 1397607 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH2:10][C@@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C@@H: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

Participants

4

Reactant 2

HCID 794712,4-Dichloro-6-methylpyrimidineHCID 70000841-Aminoindane, (S)-

Product 1

HCID 86618732HCID 86618732, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dichloro-6-methylpyrimidine (2.54 g, 0.156 mol) was dissolved in ethanol (100 mL) and N,N-Diisporopylethylamine (4.07 mL, 0.23 mol) was added followed by (S)-1-Aminoindan (2.00 mL, 0.156 mol). The solution was heated to reflux for 2 hours, TLC indicated complete conversion. The solvent was removed in vacuo and the residue was purified using chromatography on silica gel using gradient 0 to 50% ethyl acetate in hexane to afford the title compound (1.95 g, 46%). LC/MS: Rt=1.90 min, ES+ 260 (AA standard).

Workup

  1. additionN,N-Diisporopylethylamine (4.07 mL, 0.23 mol) was added
  2. temperatureThe solution was heated
  3. temperatureto reflux for 2 hours
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified

Sources & evidence

ORD record
ord-6014d405470b4076ab5c69aca090f1e3
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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