Cesium carbonate → HCID 22969110, compound

HRID 1278851Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH:9]1[CH2:13][CH2:12][CH:11]([CH2:14]Br)[O:10]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:22][C:23]1[N:31]=[C:30]2[C:26]([NH:27][CH:28]=[N:29]2)=[C:25]([Cl:32])[N:24]=1>CN(C=O)C>[CH2:1]([O:3][P:4]([CH:9]1[CH2:13][CH2:12][CH:11]([CH2:14][N:27]2[C:26]3[C:30](=[N:31][C:23]([NH2:22])=[N:24][C:25]=3[Cl:32])[N:29]=[CH:28]2)[O:10]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of (5-Bromomethyl-tetrahydro-furan-2-yl)-phosphonic acid diethyl ester (1.0, 3.32 mmol) in DMF (7mL) was transferred via cannula to a solution of cesium carbonate (1.31 g, 4.98 mmol) and 2-amino-6-chloropurine (845 mg, 4.98 mmol) in DMF (7 mL) which had been previously heated at 100° C. for 0.5 hour . The reaction mixture was stirred at 100° C. for 3 hrs. The reaction mixture was then concentrated and chromatographed, eluting with 8% methanol/dichloromethane to give [5-(2-Amino-6-chloro-purin-7-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid diethyl ester (78 mg, 6%):

Workup

concentrationThe reaction mixture was then concentrated
customchromatographed
washeluting with 8% methanol/dichloromethane

Sources & evidence

ORD record: ord-b34bbb0a4a804c4bb710780813da6ed5
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444656B1

Reaction notes

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