Formaldehyde → HCID 66953959, compound

HRID 390094Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[O:7][CH:6]([CH2:8][S:9][CH3:10])[CH:5]([CH2:11][NH:12][CH3:13])[CH2:4][O:3]1.[CH:15]1[N:16]=[C:17]2[CH2:24][CH:23]=[N:22][C:18]2=[C:19]([NH2:21])[N:20]=1.[CH2:25]=O.N.CO>O1CCOCC1.O.C(Cl)Cl>[NH3:12].[CH3:2][OH:3].[CH3:1][C:2]1([CH3:14])[O:7][CH:6]([CH2:8][S:9][CH3:10])[CH:5]([CH2:11][N:12]([CH2:25][C:24]2[C:17]3[N:16]=[CH:15][N:20]=[C:19]([NH2:21])[C:18]=3[NH:22][CH:23]=2)[CH3:13])[CH2:4][O:3]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 1-((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)-N-methylmethanamine (30 mg, 137 μmol) in dioxane (2 mL) and water (0.5 mL) was added 9-deazaadenine (27.5 mg, 205 μmol) and 37% aqueous formaldehyde (15.86 μl, 205 μmol). The reaction mixture was heated at 85° C. for 15 mins and then cooled and 7N NH3/MeOH (2.5 mL) was added. The solution was allowed to stand at RT for 3 days and concentrated to dryness. Chromatography (10% 7N NH3/MeOH in CH2Cl2) gave 7-(((((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methyl)(methyl)amino)methyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (34 mg, 93 μmol, 68% yield) as a syrup. 1H NMR (CD3OD) δ 8.16 (1H, s); 7.45 (1H, s); 3.86 (1H, dd, J=5.2, 11.9 Hz); 3.73-3.58 (3H, m); 3.52 (1H, dd, J=10.6, 11.7 Hz); 2.79 (1H, dd, J=2.5, 14.0 Hz); 2.53 (1H, dd, J=7.1, 14.0 Hz); 2.32 (1H, dd, J=5.5, 12.7 Hz); 2.24 (3H, s); 2.16 (1H, dd, J=8.1, 12.4 Hz); 2.06 (3H, s); 2.03-1.96 (1H, m); 1.36 (3H, s); 1.31 (3H. s). 13C NMR (CD3OD) δ 152.6, 151.4, 147.8, 130.6, 115.7, 113.4, 100.1, 75.9, 64.7, 57.3, 52.4, 43.6, 39.3, 38.3, 29.9, 20.4, 17.4.

Workup

temperaturecooled
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-00e649bd52b74db581f0f0d700c58a6f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383636B2

Reaction notes

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