Trifluoroacetic acid → 4-(Fluoromethyl)pyrimidin-2-amine

HRID 626694Notes

Reaction equation

HRID 626694 reaction equation
C(OC(=O)[NH:7][C:8]1[N:13]=[C:12]([CH2:14][F:15])[CH:11]=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:15][CH2:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:7])[N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69674809(4-Fluoromethylpyrimidin-2-yl)carbamic acid tert-butyl ester

Product 1

HCID 696710844-(Fluoromethyl)pyrimidin-2-amineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (4-fluoromethylpyrimidin-2-yl)carbamic acid tert-butyl ester (140 mg, 0.62 mmol) and TFA (2 mL) in DCM (2 mL) was stirred at room temperature for 1 hour then concentrated under reduced pressure. The residue was purified by SCX-2 chromatography (washing with methanol and eluting with 2M ammonia in methanol) to afford the title compound as a yellow solid (78 mg, quant. yield). 1H NMR (400 MHz, CDCl3): δ 8.34 (d, J=5.1 Hz, 1H), 6.79-6.78 (m, 1H), 5.33-5.30 (m, 1H), 5.21-5.19 (m, 1H), 5.13 (s, 2H).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was purified by SCX-2 chromatography (washing with methanol and eluting with 2M ammonia in methanol)

Sources & evidence

ORD record
ord-bb28c026ebfe4126a00d947ee664fc23
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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