Sodium cyanoborohydride → 1-(5-(3-(Trifluoromethyl)phenyl)pyrimidin-2-yl)ethanamine

HRID 1850137Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[N:11][C:12]([C:15](=O)[CH3:16])=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.[BH3-]C#[N:22].[Na+]>CCO>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[N:11][C:12]([CH:15]([NH2:22])[CH3:16])=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 120 °C

Procedure

1-(5-(3-(Trifluoromethyl)phenyl)pyrimidin-2-yl)ethanone (260 mg, 0.977 mmol), NH4OAc (1.13 g, 14.6 mmol), and NaBH3CN (245 mg, 3.91 mmol) were taken up in 8 mL 200 proof EtOH, and heated at 120° C. for 5 minutes in a microwave apparatus. The mixture was concentrated to remove the EtOH. Crude was taken up in 30 ml water+25 mL EtOAc. 6N NaOH was added until aqueous pH was ˜10. Separated layers, and extracted aqueous with EtOAc (25 ml). The combined organic layer was washed with 25 mL brine and dried with Na2SO4. Filtered and concentrated with reduced pressure to give 262 mg crude yellow oil, which was carried forward without further purification. Anal. RP-HPLC tR=0.90 min. (Column=Inertsil C8 Column, 3.0 μm, 3.0×30 mm. Column Temperature=50° C. Eluents=A: Water (5 mM Ammonium formate, 2% ACN); B: ACN. Flow Rate=2 mL/min. Gradient=0 min 5% B; 5% to 95% B in 1.70 min; 0.3 min 95% B; 2.1 min 1% B.) MS m/z 268.1 (M+H)+.

Workup

concentrationThe mixture was concentrated
customto remove the EtOH
addition6N NaOH was added until aqueous pH was ˜10
extractionSeparated layers, and extracted aqueous with EtOAc (25 ml)
washThe combined organic layer was washed with 25 mL brine
dry with materialdried with Na2SO4
filtrationFiltered
concentrationconcentrated with reduced pressure

Sources & evidence

ORD record: ord-fa9bc8d9cec4427abe4773af5516a1d4
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957068B2

Reaction notes

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