2-Methylbenzylamine → Metrifudil

HRID 1379649Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH2:9].[CH:10]1[N:15]=[C:14](Cl)[C:13]2[N:17]=[CH:18][N:19]([C@@H:20]3[O:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C@H:21]3[OH:28])[C:12]=2[N:11]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:14]1[C:13]2[N:17]=[CH:18][N:19]([C:12]=2[N:11]=[CH:10][N:15]=1)[C@@H:20]1[O:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C@H:21]1[OH:28]

Participants

Conditions

Temperature: 60 °C

Procedure

The title compound was prepared by reacting (2-methylphenyl)methylamine (1.51 g, 12.5 mmol) with 6-chloropurine riboside (2.87 g, 10.0 mmol) in dioxan (100 ml) in the presence of diisopropylethylamine (1.94 g, 15.0 mmol). The reaction mixture was heated at 60° C. for 6 h, cooled, filtered and evaporated. The residue was purified by flash chromatography, eluting initially with dichloromethane, and later increasing polarity to dichloromethanethanol (9:1), to provide the product (2.6 g, 70%) as a solid which was recrystallised from methanol to give N-[(2-methylphenyl)methyl]adenosine as white crystals (1.75 g, 47%), mp 161.5°-163.5° C., 1H NMR (DMSO-d6)δ 2.35 (3H, s, --CH3), 3.53-3.60 (1H, m, H-5'a), 3.65-3.72 (1H, m, H-5'b), 3.98 (1H, q, H-4'), 4.16 (1H, m, H-3'), 4.64 (1H, q, H-2'), 5.41 (1H, t, 5'-0H), 5.21, 5.48 (2H, 2d, 2'- and 3'-OH), 5.92 (1H, d, H-1'), 7.06-7.24 (4H, m, Ar--H), 8.20 and 8.40 (3H, s and br s, H-2, H-8 and N--H).

Workup

temperaturecooled
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography
washeluting initially with dichloromethane
temperaturelater increasing polarity to dichloromethanethanol (9:1)

Sources & evidence

ORD record: ord-24a1eaf8d4634a63a9aaf71b8fdba504
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05672588

Reaction notes

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