Sodium hydride → HCID 58174174, compound

HRID 339792Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[C:4]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:3][CH:2]=1.Cl[C:22]1[CH:27]=[N:26][CH:25]=[CH:24][N:23]=1.[H-].[Na+]>CN(C=O)C>[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[C:4]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)=[CH:16][CH:15]=2)=[N:3][CH:2]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 4-[2-(pteridin-4-ylamino)ethyl]phenol (0.267 g, 1.0 mmol) and 2-chloropyrazine (0.114 g, 1.0 mmol) in anhydrous DMF (7 mL) was added 60% sodium hydride (NaH) in mineral oil (0.060 g, 1.5 mmol) portionwise. The mixture was stirred at 55° C. overnight and then at 70° C. for a total reaction time of 32 h. The solvent was removed in vacuo and the residue was suspended in H2O. The solid was collected by suction filtration, washed with H2O and Et2O, dried in a vacuum oven at 55° C. overnight to afford pteridin-4-yl-{2-[4-(pyrazin-2-yloxy)-phenyl]-ethyl}-amine (0.291 g, 84%) as a light brown solid: 1H NMR (300 MHz, CDCl3) δ 9.02 (d, J=1.9 Hz, 1H), 8.82 (s, 1H), 8.63 (d, J=1.9 Hz, 1H), 8.43 (d, J=1.5 Hz, 1H), 8.26 (d, J=2.4 Hz, 1H), 8.10 (dd, J=2.4, 1.5 Hz, 1H), 7.33 (d, J=8.4 Hz, 2H), 7.13 (d, J=8.4 Hz, 2H), 3.99 (dd, J=13.6, 6.9 Hz, 2H), 3.08 (t, J=6.9 Hz, 2H); ESIMS m/z 346.24 ([M+H]+).

Workup

customat 70° C.
customfor a total reaction time of 32 h
customThe solvent was removed in vacuo
filtrationThe solid was collected by suction filtration
washwashed with H2O and Et2O
customdried in a vacuum oven at 55° C. overnight

Sources & evidence

ORD record: ord-9f5d186d96364589a8c8469a99857000
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895568B2

Reaction notes

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