4-Pyridinemethanamine → HCID 178506017, compound

HRID 1432385Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]([F:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[NH2:12][CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1>C(Cl)(Cl)Cl.CO>[F:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][NH:6]2)=[C:2]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[N:10]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirred solution of 6-chloro-2-fluoro-9H-purine (0.9 g, 5.22 mmol) in BunOH (60 mL) under Ar, cooled to −20° C., was added Pri2NEt (2.5 mL, 14.35 mmol) followed by 4-(aminomethyl)pyridine (0.58 mL, 5.69 mmol). The reaction mixture was stirred at-20° C. for 3 h, and then allowed to return to RT over 2 h and stirred at RT for a further 48 h, when TLC (9:1 CHCl3/MeOH) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue was purified by gradient column chromatography on silica gel, eluted with CHCl3/MeOH (100:0→90:10), to afford the title compound as a white solid (0.69 g, 54%). Mp>340° C. 1H-NMR (d6-DMSO, 250 ME): δ 4.67 (d, 2H, J=6.35 Hz, —HNCH2-Pyr), 7.34, 8.50 (2×m, 4H, Pyr), 8.14 (s, 1H, —N═CH—NH—), 8.84 (bs, 1H, —HNCH2-Pyr), 13.13 (bs, 1H, —N═CH—NH—). FAB-MS m/z (relative intensity): 245 ([M+H]+, 27), 176 (15), 154 (100), 136 (77). Accurate Mass (M+H): Actual: 245.0951, Measured: 245.0942. Microanalysis (Expected:Measured) C11H9N6F.0.6H2O: C, 51.80:52.08; H, 4.03:3.84; N, 32.95:31.29.

Workup

additionwas added Pri2NEt (2.5 mL, 14.35 mmol)
waitto return to RT over 2 h
stirringstirred at RT for a further 48 h
customThe solvent was evaporated in vacuo
customthe residue was purified by gradient column chromatography on silica gel
washeluted with CHCl3/MeOH (100:0→90:10)

Sources & evidence

ORD record: ord-2a429e4e3a654508beaf18ddbec417c3
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612079B2

Reaction notes

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