Hydrochloric Acid → 6-(Azetidin-1-ylmethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylic acid dihydrochloride

HRID 1426313Notes

Reaction equation

HRID 1426313 reaction equation
O.[OH-].[Li+].[N:4]1([CH2:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]=[C:11]([C:19]([O:21]CC)=[O:20])[CH:10]=2)[CH2:7][CH2:6][CH2:5]1.[ClH:24].C(#N)C>O1CCCC1.O>[ClH:24].[ClH:24].[N:4]1([CH2:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12]=[C:11]([C:19]([OH:21])=[O:20])[CH:10]=2)[CH2:7][CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 168937Lithium hydroxide, monohydrateHCID 58431385Ethyl 6-(azetidin-1-ylmethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate

Product 1

HCID 696731266-(Azetidin-1-ylmethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylic acid dihydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide, monohydrate (108 mg, 2.57 mmol) was added to a mixture of ethyl 6-(azetidin-1-ylmethyl)-2-(trifluoromethyl)pyrimidine-4-carboxylate (0.34 g, 1.2 mmol, from Step A) in tetrahydrofuran (6.0 mL) and water (1.5 mL). After 15 minutes, the THF was removed in vacuo and the mixture was treated with 1.0M hydrogen chloride in water (5.3 mL, 5.3 mmol), and acetonitrile (7.0 mL). The mixture was then filtered and concentrated to afford the product as a yellow solid. LCMS (M+H)+: 262.1.

Workup

  1. customthe THF was removed in vacuo
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-542c792204594e1b8036843c3d5a99af
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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