Cyanuric chloride → 4,6-dichloro-N-[(1S)-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl]-1,3,5-triazin-2-amine

HRID 1747619Notes

Reaction equation

HRID 1747619 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@@H:4]([NH2:11])[CH2:3]1.[N:13]1[C:20]([Cl:21])=[N:19][C:17](Cl)=[N:16][C:14]=1[Cl:15].CCN(C(C)C)C(C)C>C1COCC1>[Cl:15][C:14]1[N:13]=[C:20]([Cl:21])[N:19]=[C:17]([NH:11][C@@H:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:12])([CH3:1])[CH2:3]2)[N:16]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 81531DiisopropylethylamineHCID 57572827(S)-3,3-Dimethyl-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 866187194,6-dichloro-N-[(1S)-3,3-dimethyl-2,3-dihydro-1H-inden-1-yl]-1,3,5-triazin-2-amineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S)-3,3-dimethylindan-1-amine (0.67 g, 4.2 mmol) in THF (3 mL) cooled to 0° C. was added cyanuric chloride (0.874 g, 4.74 mmol) resulting in a white solid. DIPEA (0.724 mL, 4.16 mmol) was added and the yellow mixture was stirred for 1.5 hours. The reaction was quenched with H2O and extracted with DCM (3×). The combined organic layers were dried (Na2SO4), filtered and collected in vacuo to give a pale yellow oil. The residue was purified by flash chromatography (0 to 25% EtOAc/hexanes) to afford the title compound (0.771 g, 60%) as a white solid. LC/MS: Rt=2.20 min, ES+ 310 (FA standard).

Workup

  1. customresulting in a white solid
  2. customThe reaction was quenched with H2O
  3. extractionextracted with DCM (3×)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customcollected in vacuo
  7. customto give a pale yellow oil
  8. customThe residue was purified by flash chromatography (0 to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a17c2495a117430c8fdd6f7ee5016dfd
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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