Ammonia → HCID 19993492, compound

HRID 345081Notes

Reaction equation

C([O:3][P:4]([CH2:9][O:10][CH2:11][CH:12]([O:15][N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:25])[CH2:13][OH:14])([O:6]CC)=[O:5])C.Br[Si](C)(C)C.N>CN(C)C=O>[OH:14][CH2:13][CH:12]([O:15][N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:25])[CH2:11][O:10][CH2:9][P:4]([OH:5])([OH:6])=[O:3]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 9-(1-diethoxyphosphorylmethoxy-3-hydroxyprop-2-oxy)adenine (100 mg, 0.27 mmol) in N,N-dimethylformamide (5 ml) was treated with bromotrimethylsilane (0.36 ml, 2.7 mmol) and stirred for 16 hours at 20° C. After this time, t.l.c. (isopropyl alcohol-water-0.88 ammonia, 60:30:10) showed some monoester still present. More bromotrimethylsilane (0.18 ml, 1.35 mmol) was added and the reaction mixture stirred at 20° C. for 2 hours. The solvent was evaporated and the residual brown oil chromatographed on reverse-phase silica, eluting with water, affording 9-(1-hydroxy-3-phosphonomethoxyprop-2-oxy)adenine (65 mg, 76%) as a white solid; m.p. 222°-225° C.; λmax (H2O) 259(ε12,600)nm; νmax (KBr) 3420, 1700, 1650, 1620, 1120, and 1060 cm-1 ; δH [(CD3)2SO] 2.7-4.2(3H, v.br.s, D2O exchangeable, 3 ×OH), 3.64(2H, dJ8.5 Hz, CH2P), 3.67(2H, d, J4.9 Hz, CH2OH), 3.81(2H, d, J4.9 Hz,CH2OCH2P), 4.47(1H, m, CHON), 7.43(2H, br.s, D2O exchangeable, NH2), 8.16(1H, s, H 2/H-8), 8.35(1H, s, H-2/H-8); m/z(FAB+veIon) 320(M+, 100%), 342(MNa+, 24%); Found: C,31 77; H,4.67; N.20.83%; C9H14N5O6P.1.0H2O requires C,32.05; H,4.78; N,20.77%.

Workup

stirringthe reaction mixture stirred at 20° C. for 2 hours
customThe solvent was evaporated
customthe residual brown oil chromatographed on reverse-phase silica
washeluting with water

Sources & evidence

ORD record: ord-e7cdbf6d4b4340c9a2b6e24a4e7b7614
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05055458

Reaction notes

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