Trimethylamine → HCID 136383553, compound

HRID 1278852Notes

Reaction equation

HRID 1278852 reaction equation
[CH2:1]([O:3][P:4]([CH:9]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][C:18]([NH2:25])=[N:19][C:20]=3Cl)[O:10]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].CN(C)C.N1C(=[O:40])C2NC=NC=2N=C1N>O.C1COCC1>[CH2:1]([O:3][P:4]([CH:9]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH:23]=[N:22][C:21]3[C:20](=[O:40])[NH:19][C:18]([NH2:25])=[N:17][C:16]2=3)[O:10]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

6

Reactant 3

HCID 1146TrimethylamineHCID 21255837HCID 21255837, compoundHCID 135398634Guanine

Product 1

HCID 136383553HCID 136383553, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To [5-(2-Amino-6-chloro-purin-9-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid diethyl ester (100 mg, 0.25 mmol) in water (7 mL) and THF (5 mL) was added trimethylamine (1.6 mL, 6.4 mmol). The reaction mixture was stirred at RT under nitrogen overnight. Conversion to guanine was confirmed by UV spectroscopy. The THF was removed in vacuo and the reaction mixture lyophilized. The sample was chromatographed eluting with 10% methanol/dichloromethane to give [5-(2-Amino-6-oxo-1,6-dihydro-purin-9-ylmethyl)-tetrahydro-furan-2-yl]-phosphonic acid diethyl ester as a white powder (40 mg, 42%).

Workup

  1. customThe THF was removed in vacuo
  2. customThe sample was chromatographed
  3. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-e66f21da8a85413dba188452156bb366
Source dataset
uspto-grants-2002_09
Patent number
US06444656B1

Reaction notes

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