Hydrochloric Acid → (1R,2S,3R,5R)-3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

HRID 1054520Notes

Reaction equation

HRID 1054520 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@@H:9]2[CH2:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]2[OH:17])[C:3]=1[CH2:18][CH:19](OCC)OCC.Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]2[CH:18]=[CH:19][N:8]([C@@H:9]3[CH2:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]3[OH:17])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86666111(1R,2S,3R,5R)-3-((6-chloro-5-(2,2-diethoxyethyl)pyrimidin-4-yl)amino)-5-(hydroxymethyl)cyclopentane-1,2-diol

Product 1

HCID 86666112(1R,2S,3R,5R)-3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of crude (1R,2S,3R,5R)-3-((6-chloro-5-(2,2-diethoxyethyl)pyrimidin-4-yl)amino)-5-(hydroxymethyl)cyclopentane-1,2-diol in 1,4-dioxane (160 mL) was treated with a 1 M aqueous solution of HCl (30 mL, 30 mmol) and stirred at rt for 69.5 h; HPLC indicated clean conversion to one product, LC MS showed mass for desired product. The reaction mixture was neutralized with concentrated NH4OH (to pH 7) and the volatiles were removed in vacuo to afford a brown slurry, which was carried on without further purification: MS (ESI+) for C12H14ClN3O3 m/z 284.1 (M+H)+; MS (ESI−) for C12H14ClN3O3 m/z 282.2 (M−H)−, 328.2 (M+HCO2)−; HPLC purity>95% (ret. time, 1.947 min). Variation on route from J. Med. Chem. 10, 665 (1967).

Sources & evidence

ORD record
ord-c42140f8ba12439d879f2bfffaa08c95
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

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