Cyclopentylamine → N2-cyclopentyl-5-iodo-N4-(6-methoxypyridin-3-yl)pyrimidine-2,4-diamine

HRID 1621536Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[C:5]([I:17])=[CH:4][N:3]=1.[CH:18]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C>[CH:18]1([NH:23][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)[C:5]([I:17])=[CH:4][N:3]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

Conditions

Temperature: 140 °C

Procedure

A glass microwave reaction vessel was charged with 2-chloro-5-iodo-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine (181 mg, 0.499 mmol), cyclopentylamine (85 mg, 0.998 mmol) and ethanol (3 mL). The reaction mixture was stirred and heated in a Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 140° C. for 30 min. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 50% EtOAc/hexanes to give N2-cyclopentyl-5-iodo-N4-(6-methoxypyridin-3-yl)pyrimidine-2,4-diamine (188 mg, 0.457 mmol, 92% yield). 1H NMR (300 MHz, CDCl3) δ 8.30 (s, 1H); 8.14 (s, 1H); 7.82 (d, J=10.38 Hz, 1H); 6.75 (d, J=8.92 Hz, 1H); 6.66 (s, 1H); 4.79-4.96 (m, 1H); 4.10 (dd, J=13.15, 4.53 Hz, 1H); 3.94 (s, 3H); 1.97 (dd, J=11.62, 5.19 Hz, 2H); 1.56-1.78 (m, 4H); 1.35-1.50 (m, 2H). m/z (ESI, +ve ion) 412.0 (M+H)+.

Workup

customA glass microwave reaction vessel
customThe solvent was removed in vacuo
customthe residue was purified by silica gel chromatography
washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record: ord-04f9c78b367545bc95c354e9e0fcca06
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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