Potassium Iodide → HCID 60163220, compound

HRID 243282Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[C:11](=[O:12])[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl[CH2:14][C:15]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]2[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=2[N:16]=1.C([O-])([O-])=O.[Cs+].[Cs+].[I-].[K+]>CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:11](=[O:12])[CH:10]=[CH:9][N:8]([CH2:14][C:15]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18]4[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=4[N:16]=3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-amino-8H-pyrido[2,3-d]pyrimidin-5-one (35 mg, 0.214 mmol), 2-chloromethyl-1-phenyl-1H-benzoimidazole (52 mg, 0.214 mmol), Cs2CO3 (105 mg, 0.321 mmol) and potassium iodide (4 mg, 0.021 mmol) in DMF (1 mL) was stirred for 3 h in a sealed tube at 130° C. Volatiles were then removed under reduced pressure and the residue suspended in DCM and filtered. The filtrate was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) and the resulting material was triturated with diethyl ether affording 111 as a pale yellow solid (28 mg, 36%). LCMS: RT 3.47 min [M+H]+ 369.1. 1H NMR (CDCl3, 400 MHz): δ 9.76 (1H, bs), 8.07 (1H, s), 7.82-7.77 (1H, m), 7.65 (1H, d, J=7.97 Hz), 7.50-7.44 (3H, m), 7.34-7.23 (4H, m), 7.14-7.09 (1H, m), 6.28 (1H, d, J=7.97), 5.86-5.78 (1H, m), 5.63 (2H, s)

Workup

customVolatiles were then removed under reduced pressure
filtrationfiltered
customThe filtrate was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)
customthe resulting material was triturated with diethyl ether affording 111 as a pale yellow solid (28 mg, 36%)

Sources & evidence

ORD record: ord-a00ce3ee66594f499f41f8dadf85859b
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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