Dimethyl Sulfoxide → 1-Cyclopropyl-3-[4-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl]urea

HRID 853304Notes

Reaction equation

[CH:1]1([NH:4][C:5](=O)[O:6]C2C=CC=CC=2)[CH2:3][CH2:2]1.CS(C)=O.[C:18]1([C:24]2[NH:40][C:27]3[N:28]=[CH:29][N:30]=[C:31]([O:32][C:33]4[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=4)[C:26]=3[CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH:1]1([NH:4][C:5]([NH:39][C:36]2[CH:37]=[CH:38][C:33]([O:32][C:31]3[C:26]4[CH:25]=[C:24]([C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)[NH:40][C:27]=4[N:28]=[CH:29][N:30]=3)=[CH:34][CH:35]=2)=[O:6])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

After adding 30 mg of phenyl cyclopropylcarbamate and 0.5 ml of dimethylsulfoxide to 40 mg of 4-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenylamine, the mixture was stirred at 80° C. for 4 hours. The mixture was returned to room temperature, water was added, liquid separation and extraction were performed with ethyl acetate, and the solid obtained by concentration to dryness was washed with ether to obtain 6 mg of the title compound. p 1H-NMR Spectrum: (DMSO-d6) 0.30–0.40 (2H, m), 0.55–0.65 (2H, m), 2.43–2.57 (1H, m, coverd by DMSO peak), 6.20 (1H, brs), 6.60 (2H, d, J=8.90 Hz), 6.83 (1H, s), 6.87–6.91 (1H, m), 7.10–7.16 (1H, m), 7.30–7.50 (3H, m), 7.90 (2H, d, J=8.1 Hz), 8.26 (1H, d, J=0.4 Hz), 8.92 (1H, brs,), 12.60 (1H, brs)

Workup

customwas returned to room temperature
customliquid separation and extraction
customthe solid obtained by concentration to dryness
washwas washed with ether

Sources & evidence

ORD record: ord-37a732f4108a4dc2be09906903ea879c
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253286B2

Reaction notes

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