Ammonia methanol → HCID 66953614, compound

HRID 390072Notes

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][CH2:22][C@H:23]([OH:27])[CH2:24][S:25][CH3:26])=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:28].CO>>[NH2:28][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][CH2:22][C@H:23]([OH:27])[CH2:24][S:25][CH3:26])[C:13]=2[N:14]=[CH:15][N:16]=1

Participants

Reactant 2

HCID 21705897Ammonia methanol

HCID 86651325HCID 86651325, compound

Product 1

HCID 66953614HCID 66953614, compoundYield 72%

Procedure

The product from Example 2.4 (0.124 g, 0.305 mmol) was stirred in a solution of 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 in MeOH, 98:2) to give (S)-1-((4-amino-5-(benzyloxymethyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-3-(methylthio)propan-2-ol (0.085 g, 72%) as a colourless gum. 1H NMR (CD3OD) δ 8.16 (s, 1H), 7.47 (s, 1H), 7.28 (m, 5H), 5.66 (s, 2H), 4.58 (s, 2H), 3.97 (d, J=13.8 Hz, 1H), 3.91-3.83 (m, 2H), 2.84 (dd, J=12.1, 3.5 Hz, 1H), 2.62 (dd, J=12.1, 8.4 Hz, 1H), 2.56 (d, J=6.4 Hz, 2H), 2.09 (s, 3H). 13C NMR (CD3OD) δ 152.8, 151.6, 149.4, 137.7, 133.5, 129.5, 129.3, 129.2, 116.0, 114.3, 78.6, 71.4, 70.3, 54.6, 43.3, 40.4, 16.2. +ESMS Found 388.1813 (M+H)+ C19H26N5O2S requires 388.1807.

Workup

customwas evaporated
customthe residue chromatographed on silica gel (CH2Cl2-7M NH3 in MeOH, 98:2)

Sources & evidence

ORD record: ord-670829faaba341f2a3e42d0fe39f8b4b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383636B2

Reaction notes

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