Potassium Carbonate → HCID 21097912, compound

HRID 1351119Notes

Reaction equation

[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[C:12]#[C:13][C:14]1[N:22]=[C:21]3[C:17]([NH:18][CH:19]=[N:20]3)=[C:16]([NH2:23])[N:15]=1)[CH2:9]2.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:41][CH:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)(=O)=O)=CC=1>CN(C=O)C>[CH:42]1([CH2:41][N:20]2[CH:19]=[N:18][C:17]3[C:21]2=[N:22][C:14]([C:13]#[C:12][CH:3]2[CH:4]4[CH2:5][CH:6]5[CH2:7][CH:8]([CH2:9][C:2]2([OH:1])[CH2:11]5)[CH2:10]4)=[N:15][C:16]=3[NH2:23])[CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

Conditions

Temperature: 70 °C

Procedure

2-{2-[Hydroxy-adamantan-2-yl]ethyn-1-yl}adenine (44 mg, 0.1422 mmol) was dissolved in DMF (20 mL) with heating. Anhydrous potassium carbonate (51 mg, 0.3690 mmol) and cyclopentylmethyl 4-methylbenzenesulfonate (54 mg, 0.2123 mmol) were added and the mixture stirred at 70° C. for 72 h. Extra cyclopentylmethyl 4-methylbenzenesulfonate (82 mg, 0.3224 mmol) was added and stirring continued at 100° C. a further 4.5 h. The reaction mixture was adhered to silica and purified by column chromatography, eluting with a gradient of DCM/MeOH (0–6%) to afford the pure 47 as a white solid: yield 38 mg, 68%. 1H NMR (CD3OD) δ 8.15 (s, 1H), 4.14 (d, 2H, J=7.7 Hz), 2.48 (quintet, 1H, J=7.5 Hz), 2.37–2.22, 2.08–2.02, 1.89–1.58, 1.37–1.24 (4×m, 22H). LRMS ESI (M+H+) 392.0.

Workup

temperaturewith heating
stirringstirring
waitcontinued at 100° C. a further 4.5 h
custompurified by column chromatography
washeluting with a gradient of DCM/MeOH (0–6%)

Sources & evidence

ORD record: ord-0ad8909f12554786b9e744aa84766dc2
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217702B2

Reaction notes

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