Trifluoroacetic acid → 6-[(E)-2-cyclopropylvinyl]pyrimidin-4-amine

HRID 1050334Notes

Reaction equation

[CH:1]1(/[CH:4]=[CH:5]/[C:6]2[N:11]=[CH:10][N:9]=[C:8]([NH:12]C(=O)OC(C)(C)C)[CH:7]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1(/[CH:4]=[CH:5]/[C:6]2[N:11]=[CH:10][N:9]=[C:8]([NH2:12])[CH:7]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of tert-butyl N-[6-[(E)-2-cyclopropylvinyl]pyrimidin-4-yl]carbamate (3, 350 mg, 1.34 mmol) in dichloromethane (10 mL) at 0° C., trifluoroacetic acid (1.5 mL, 1.34 mmol) was added and stirred at 25° C. for 16 h. The solvent was removed under reduced pressure and the mixture made basic with the residue with aqueous ammonia. Filtration and washing with diethyl ether provided (6-[(E)-2-cyclopropylvinyl]pyrimidin-4-amine (4) as a brown solid. Yield: 170 mg, 79%; MS (ESI) m/z 162.10 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 8.19 (s, 1H), 6.70 (brs, 2H), 6.32-6.27 (m, 2H), 6.17 (s, 1H), 1.60 (m, 1H), 0.84 (m, 2H), 0.55 (m, 2H).

Workup

customThe solvent was removed under reduced pressure
filtrationFiltration
washwashing with diethyl ether

Sources & evidence

ORD record: ord-4b809c855a9e4cdea7c5b1345d1fe163
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382248B2

Reaction notes

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