Ammonia methanol → HCID 66953593, compound

HRID 390079Notes

Reaction equation

[CH2:1]([O:8][CH2:9][N:10]1[C:18]2[C:17](Cl)=[N:16][CH:15]=[N:14][C:13]=2[C:12]([CH2:20][NH:21][C@@H:22]([C@H:25]([OH:29])[CH2:26][S:27][CH3:28])[CH2:23][OH:24])=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:30].CO>>[NH2:30][C:17]1[C:18]2[N:10]([CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:11]=[C:12]([CH2:20][NH:21][C@@H:22]([C@H:25]([OH:29])[CH2:26][S:27][CH3:28])[CH2:23][OH:24])[C:13]=2[N:14]=[CH:15][N:16]=1

Participants

Reactant 2

HCID 21705897Ammonia methanol

HCID 86651327HCID 86651327, compound

Product 1

HCID 66953593HCID 66953593, compoundYield 60%

Procedure

The product from Example 6.7 (0.19 g, 0.435 mmol) was stirred in 7M NH3-MeOH (25 ml) for 24 h in a sealed tube at 135° C. (oil bath). After cooling to rt the solvent was evaporated and the residue chromatographed on silica gel (CH2Cl2-7M NH3-MeOH 96.5:3.5 then 95:5) to give (2R,3S)-2-((4-amino-5-(benzyloxymethyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-4-(methylthio)butane-1,3-diol (0.108 g, 60%) as a yellow gum. 1H NMR (CD3OD) δ 8.17 (s, 1H), 7.46 (s, 1H), 7.28 (m, 5H), 5.63 (s, 2H), 4.57 (s, 2H), 4.07 (d, J=13.7 Hz, 1H), 3.91 (d, J=13.7 Hz, 1H), 3.81-3.73 (m, 2H), 3.64 (dd, J=11.4, 5.0 Hz, 1H), 2.81-2.69 (m, 2H), 2.54 (dd, J=13.5, 7.4 Hz, 1H), 2.04 (s, 3H). 13C NMR (CD3OD, referenced to the centre line of CD3OD at 49.0 ppm) δ 152.8, 151.5, 149.4, 137.8, 133.6, 129.5, 129.3, 129.2, 116.2, 115.1, 78.6, 71.4, 71.3, 62.1, 62.0, 42.0, 39.3, 16.0. +ESMS Found 418.1907 (M+H)+ C20H28N5O3S requires 418.1913.

Workup

customwas evaporated
customthe residue chromatographed on silica gel (CH2Cl2-7M NH3-MeOH 96.5:3.5

Sources & evidence

ORD record: ord-f156246e20584d749fcc13a309e1caed
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383636B2

Reaction notes

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