Diisopropylethylamine → ((3aR,4R,6R,6aR)-6-{6-[(1S)-2,3-dihydro-1H-inden-1-yl(methyl)amino]-9H-purin-9-yl}-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

HRID 552763Notes

Reaction equation

[CH3:1][NH:2][C@@H:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.C(NS(=O)(=O)[O:33][CH2:34][C@@H:35]1[C@@H:42]2[C@@H:38]([O:39][C:40]([CH3:44])([CH3:43])[O:41]2)[C@H:37]([N:45]2[CH:53]=[N:52][C:51]3[C:46]2=[N:47][CH:48]=[N:49][C:50]=3Cl)[O:36]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCN(C(C)C)C(C)C>C(O)C>[C@@H:3]1([N:2]([CH3:1])[C:50]2[N:49]=[CH:48][N:47]=[C:46]3[C:51]=2[N:52]=[CH:53][N:45]3[C@H:37]2[C@@H:38]3[O:39][C:40]([CH3:44])([CH3:43])[O:41][C@@H:42]3[C@@H:35]([CH2:34][OH:33])[O:36]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of (1S)-N-methylindan-1-amine (67.8 mg, 0.461 mmol), [(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl tritylsulfamate (200 mg, 0.309 mmol) and DIPEA (0.160 mL, 0.919 mmol) in ethanol (3.0 mL) was heated at 150° C. for 600 s using microwave irradiation. The residue was purified via flash chromatography (0 to 100% EtOAc/DCM) to afford the title compound as a brown oil (74.3 mg, 55%).

Workup

custommicrowave irradiation
customThe residue was purified via flash chromatography (0 to 100% EtOAc/DCM)

Sources & evidence

ORD record: ord-eba6efda2536485e82857e7914e5d618
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951810B2

Reaction notes

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