Water → 2-Chloro-6-benzylamino-9-(2-propynyl)purine

HRID 870309Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]#[CH:27].O>CS(C)=O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:27][C:26]#[CH:25])=[C:4]([NH:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-chloro-6-benzylaminopurine (1.1 g, 3.8 mmol), in DMSO (5 mL) was cooled to 0° C., potassium carbonate (0.79 g, 5.7 mmol) and propargyl bromide (0.45 g, 3.8 mmol) was added to the contents, and stirred for 1 h at 0° C. Water (20 mL) was then added to the reaction mixture, and the resulting yellow precipitate was filtered and washed with excess water (50 mL). Compound 5 (1.1 g, 80%) was obtained as an off-white solid upon successive recrystallization from dichloromethane and ethyl acetate: mp 180° C.; EI/MS (m/z (relative %)): 297 (63, M+.), 298 (15), 299 (23), 258 (46), 91(100); 1H NMR (400 MHz, DMSO) δ 8.23 (s, 1H), 7.21-7.38 (m, 5H), 5.03 (bs, 2H), 4.62 (d, J=6 Hz, 2H), 3.51 (s, 1H). 13C NMR (100 MHz, DMSO) δ 155.6 (s), 154.0 (s), 150.3 (s), 140.7 (d, 1JC—H=214 Hz) 139.9 (s), 128.9 (d, 1JC—H=159 Hz), 127.9 (d, 1JC—H=157 Hz), 126.8 (d, 1JC—H=158 Hz), 118.1 (s), 78.5 (t, 2JC—H=9 Hz) 76.7 (dt, 1JC—H=252 Hz, 3JC—H=4 Hz), 43.8 (t, 1JC—H=126 Hz), 33.3 (t, 1JC—H=139 Hz).

Workup

filtrationthe resulting yellow precipitate was filtered
washwashed with excess water (50 mL)

Sources & evidence

ORD record: ord-fabff4403d174c57a6100b6d174cf6d0
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969556B2

Reaction notes

Loading…