2-(Furan-2-yl)ethan-1-amine → 5-Bromo-2-(2-fur-2-ylethylamino)-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine

HRID 2111666Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH:16][C:17]2[CH:21]=[C:20]([CH3:22])[NH:19][N:18]=2)=[N:4][C:5]([NH:8][CH2:9][C:10]2ON=[C:12]([CH3:15])[CH:11]=2)=[N:6][CH:7]=1.NCC[C:26]1[O:27]C=CC=1>C(O)CCC>[Br:1][C:2]1[C:3]([NH:16][C:17]2[CH:21]=[C:20]([CH3:22])[NH:19][N:18]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][C:11]2[O:27][CH:26]=[CH:15][CH:12]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-bromo-2-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Method 1; 290 mg, 11.0 mmol), 2-(2-aminoethyl)furan (330 mg, 3.0 mmol) and 1-butanol (5 ml) was heated at 120° C. for 5 hours. The mixture was allowed to cool to ambient temperature and the volatiles removed by evaporation. The residue was dissolved in DCM and washed with water followed by brine. The organics were separated, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether, the solid product collected and purified by column chromatography on silica gel eluting with DCM/methanol (95:5) to give the titled compound (80 mg, 22%). 1H NMR (DMSO): δ 2.1 (s, 3H), 2.85 (m, 2H), 3.45 (m 2H), 6.10 (m, 1H), 6.35 (m, 1H), 6.4 (br s, 1H), 7.15 (br s, 1H), 7.5 (s, 1H), 8.0 (br s, 2H), 12.05 (br s, 1H); MS: m/z 363.

Workup

temperatureto cool to ambient temperature
customthe volatiles removed by evaporation
dissolutionThe residue was dissolved in DCM
washwashed with water
customThe organics were separated
dry with materialdried (MgSO4)
customthe solvent removed by evaporation
customThe residue was triturated with ether
customthe solid product collected
custompurified by column chromatography on silica gel eluting with DCM/methanol (95:5)

Sources & evidence

ORD record: ord-f1f374a4c88245bab87ffeae28d1d9ba
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521453B2

Reaction notes

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