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

HRID 1678004Notes

Reaction equation

HRID 1678004 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.C(N(CC)C(C)C)(C)C.[NH2:19][C@@H:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:19][C@@H:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21]2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 794712,4-Dichloro-6-methylpyrimidineHCID 81531DiisopropylethylamineHCID 70000841-Aminoindane, (S)-

Product 1

HCID 86618732HCID 86618732, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dichloro6-methylpyrimidine (2.54 g, 0.156 mol) was dissolved in ethanol (100 mL) and N,N-diisopropylethylamine (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. temperatureThe solution was heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified

Sources & evidence

ORD record
ord-411693de4eb5419cbbcc33a5c0ca4d86
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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