Dimethylformamide → HCID 118162204, compound

HRID 1749422Notes

Reaction equation

HRID 1749422 reaction equation
CC[N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])C.Cl[C:11]1[N:16]=[C:15]([Cl:17])[C:14]([C:18]([F:21])([F:20])[F:19])=[CH:13][N:12]=1.C[N:23]([CH:25]=O)C>>[Cl:17][C:15]1[C:14]([C:18]([F:21])([F:20])[F:19])=[CH:13][N:12]=[C:11]([NH:23][CH2:25][C:9]2[CH:7]=[N:3][CH:4]=[CH:6][C:14]=2[C:18]([F:21])([F:20])[F:19])[N:16]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidine

Product 1

HCID 118162204HCID 118162204, compoundYield 17.2%

Conditions

Temperature
0 °C

Procedure

(4-(Trifluoromethyl)pyridin-3-yl)methanamine, HCl (1.0 equiv.) was placed in a round bottom flask with DIEA (2.5 M) and DMF (0.6 M). The flask was cooled to 0° C. and 2,4-dichloro-5-(trifluoromethyl)pyrimidine (1.0 equiv.) was slowly added portion-wise. The reaction mixture was stirred overnight and allowed to warm to room temperature. The reaction mixture was loaded directly onto a silica gel column and purified using 0-20% ethyl acetate in hexanes followed by 20% ethyl acetate in hexanes. Fractions containing the desired isomer (lower Rf spot by thin layer chromatography) were combined and volatile organic solvents were removed under reduced pressure to give 4-chloro-5-(trifluoromethyl)-N-((4-(trifluoromethyl)pyridin-3-yl)methyl)pyrimidin-2-amine (17.2% yield) as a white solid. MS (ESI) m/z 357.2 [M+1]+

Workup

  1. temperatureto warm to room temperature
  2. custompurified
  3. additionFractions containing the desired isomer (lower Rf spot by thin layer chromatography)
  4. customvolatile organic solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-8ca9d4ac91a8407f8f2e476586a15ef9
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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