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

HRID 5954Notes

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 filtrater 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 filtrater concentrated in vacuo

Sources & evidence

ORD record: ord-048b5067c6284c43800165c2eb0e4b52
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246931

Reaction notes

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