Thionyl Chloride → rac-N-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl]-5-(chloromethyl)-4-(trifluoromethyl)pyrimidin-2-amine

HRID 38770Notes

Reaction equation

HRID 38770 reaction equation
[C@H:1]12[CH2:7][C@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[NH:8][C:9]1[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([CH2:19]O)=[CH:11][N:10]=1.S(Cl)([Cl:23])=O.C(=O)([O-])O.[Na+]>ClCCl>[C@H:1]12[CH2:7][C@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[NH:8][C:9]1[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]([CH2:19][Cl:23])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66720204rac-{2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]-4-(trifluoromethyl)pyrimidin-5-yl}methanol

Product 1

HCID 66720336rac-N-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl]-5-(chloromethyl)-4-(trifluoromethyl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of rac-{2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]-4-(trifluoromethyl)pyrimidin-5-yl}methanol (1.05 g) and dichloromethane (21 mL) was added thionyl chloride (0.8 mL) under ice-cooling, followed by stirring under ice-cooling for 30 minutes and at room temperature for 1 hour. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution under ice-cooling, followed by stirring for 10 minutes. The reaction mixture was extracted with chloroform and the obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain rac-N-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl]-5-(chloromethyl)-4-(trifluoromethyl)pyrimidin-2-amine (1.06 g) as a pale yellow solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring for 10 minutes
  4. extractionThe reaction mixture was extracted with chloroform
  5. dry with materialthe obtained organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-46f3b85d2d4044e48e773ed11823f60d
Source dataset
uspto-grants-2013_09
Patent number
US08524727B2

Reaction notes

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