Benzylamine → N-Benzyl-2-chloro-9H-purin-6-amine

HRID 870308Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 2,6-dichloropurine (110 mg, 0.52 mmol) in n-butanol (3 mL), benzylamine (57 mg, 0.52 mmol) and triethylamine (72 mg, 0.79 mmol) was added. The mixture was stirred and heated at 60° C. for 15 min. The resulting precipitate was filtered, washed with water (20 mL) and methanol (10 mL), and air-dried overnight. Compound 4 (130 mg, 95%) was obtained as an off-white solid: mp 262° C.; EI/MS (m/z (relative %)): 259 (19, M+.), 260 (14), 261 (17%), 106 (100), 91 (77); 1H NMR (400 MHz, DMSO) δ 8.15 (s, 1H), 7.25-7.34 (m, 5H), 4.66 (d, J=6 Hz, 2H); 13C NMR (100 MHz, DMSO) δ 155.0 (s) 153.1 (s), 150.7 (s), 140.2 (d, 1JC—H=200 Hz), 139.6 (s), 128.5 (d, 1JC—H=158 Hz, 127.5 (d, 1JC—H=157 Hz), 127.0 (d, 1JC—H=158 Hz) 118.1 (s), 43.4 (t, 1JC—H=139 Hz).

Workup

additionwas added
filtrationThe resulting precipitate was filtered
washwashed with water (20 mL) and methanol (10 mL)
customair-dried overnight

Sources & evidence

ORD record: ord-ae06ce0865334ccabbecdd46fe99ac85
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969556B2

Reaction notes

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