9-(2-Methoxycarbonyl-1-cyclobutyl)adenine → 9-(2-Hydroxymethyl-1-cyclobutyl)adenine

HRID 465749Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH2:8][CH2:7][CH:6]1[N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:18])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:2][CH2:3][CH:5]1[CH2:8][CH2:7][CH:6]1[N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:18]

Participants

Conditions

Temperature: 0 °C

Procedure

9-(2-methoxycarbonyl-1-cyclobutyl)adenine (500 mg, 2.02 mmol) from Step A was dissolved in 250 mL of THF and the solution was cooled to 0° C. with stirring under a nitrogen atmosphere. Lithium aluminum hydride (115 mg, 3.03 mmol) was added and the reaction mixture was stirred for 30 minutes then quenched with 115 μL of water followed by 115 μL of 15% sodium hydroxide and 345 μL of water. The reaction mixture was filtered through Celite filter aid. The Celite was washed with ethyl acetate and the filtrate concentrated in vacuo to give 430 mg (97% yield) of the title compound; MS DCI-NH3M/Z: 220 (M+H)+ ; 1H NMR (d6-DMSO) δ 1.65 (m, 1H), 1.90 (m, 1H), 2.32 (m, 1H), 2.50 (m, 1H), 3.10 (m, 1H), 3.47 (t, 2H), 4.67-4.77 (m, 2H, H-1'+OH), 7.20 (bs, 2H), 8.12 (s, 1H), 8.27 (s, 1H); Analysis calculated for C10H13N5O: C, 54.78; H, 5.98; N, 31.95. Found: C, 54.79; H, 6.01; N, 31.66.

Workup

stirringthe reaction mixture was stirred for 30 minutes
customthen quenched with 115 μL of water
filtrationThe reaction mixture was filtered through Celite
filtrationfilter aid
washThe Celite was washed with ethyl acetate
concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record: ord-91817d53e11a444faf76e78b4e08855e
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05153352

Reaction notes

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