5-Amino-4,6-dichloropyrimidine → (1R,2S,3R,5R)-3-((5-amino-6-chloropyrimidin-4-yl)amino)-5-(hydroxymethyl)cyclopentane-1,2-diol

HRID 511561Notes

Reaction equation

HRID 511561 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][C@H:6]([CH2:8][OH:9])[C@@H:5]([OH:10])[C@H:4]1[OH:11].[Cl:12][C:13]1[C:18]([NH2:19])=[C:17](Cl)[N:16]=[CH:15][N:14]=1>C(O)C>[NH2:19][C:18]1[C:17]([NH:2][C@@H:3]2[CH2:7][C@H:6]([CH2:8][OH:9])[C@@H:5]([OH:10])[C@H:4]2[OH:11])=[N:16][CH:15]=[N:14][C:13]=1[Cl:12]

Participants

4

Reactant 2

HCID 794345-Amino-4,6-dichloropyrimidineHCID 2734536(1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol Hydrochloride

Product 1

HCID 10978690(1R,2S,3R,5R)-3-((5-amino-6-chloropyrimidin-4-yl)amino)-5-(hydroxymethyl)cyclopentane-1,2-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (16.9 g, 45.1 mmol) and 4,6-dichloropyrimidin-5-amine (5.7 g, 35 mmol) in ethanol (45 mL) was evenly distributed amongst three tubes and subjected to microwave conditions (CEM apparatus, 300 W max, 150° C. max, 250 psi max, 3 min ramp, 30 min hold) to afford brown solutions; HPLC/LC MS indicated conversion to the desired product. The three reaction mixtures were combined and concentrated in vacuo to afford the crude title compound as a dark brown oil, which was concentrated from toluene (2×30 mL) and carried on without purification: MS (ESI+) for C10H15ClN4O3 m/z 275.0 (M+H)+; MS (ESI−) for C10H15ClN4O3 m/z 273.0 (M−H)−.

Workup

  1. customsubjected to microwave conditions (CEM apparatus, 300 W max, 150° C. max, 250 psi max, 3 min ramp, 30 min hold)
  2. customto afford brown solutions

Sources & evidence

ORD record
ord-a01087bef4e34f7ca1be3110e7efcd8d
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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