(R)-(-)-1-Aminoindan → HCID 89825842, compound

HRID 2206846Notes

Reaction equation

HRID 2206846 reaction equation
F[C:2]1[CH:3]=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[C@H:12]1([NH2:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1.C1(C(N)C2CCCCC2)CCCCC1>CN1CCCC1=O>[C@H:12]1([NH:21][C:2]2[CH:3]=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 2733933(R)-(-)-1-AminoindanHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 137542555-Fluoro-2-(trifluoromethyl)pyrimidine

Product 1

HCID 89825842HCID 89825842, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.20 g (1.20 mmol) of 5-fluoro-2-(trifluoromethyl)pyrimidine, 0.225 g (1.69 mmol) of (1R)-2,3-dihydro-1H-inden-1-amine and 0.50 g (2.41 mmol) of dicyclohexylmethylamine in 1.5 ml of 1-methyl-2-pyrrolidone are heated in a closed cuvette in the microwave at 180° C. for 120 minutes (Biotage Initiator, http://www.biotage.com/DynPage.aspx?id=22001). The crude mixture obtained in this manner is applied to silica gel and purified by column chromatography using the mobile phase heptane/ethyl acetate. Concentration gives 0.34 g of N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2-(trifluoromethyl)pyrimidine-5-amine (melting point 123.7° C., yield 96% at a purity of 95%).

Workup

  1. customThe crude mixture obtained in this manner
  2. custompurified by column chromatography
  3. concentrationConcentration

Sources & evidence

ORD record
ord-b6033d8162e7421e8f0043ba556f7773
Source dataset
uspto-grants-2016_06
Patent number
US09375002B2

Reaction notes

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