Benzyl chloroformate → HCID 178469708, compound

HRID 2189010Notes

Reaction equation

HRID 2189010 reaction equation
Cl.Cl.[NH2:3][C:4]1[NH:5][C:6]2[NH:7][CH2:8][CH:9]([CH:15]([OH:19])[CH:16]([OH:18])[CH3:17])[NH:10][C:11]=2[C:12](=[O:14])[N:13]=1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>N1C=CC=CC=1>[CH2:24]([O:23][C:21]([N:10]1[CH:9]([CH:15]([OH:19])[CH:16]([OH:18])[CH3:17])[CH2:8][NH:7][C:6]2[NH:5][C:4]([NH2:3])=[N:13][C:12](=[O:14])[C:11]1=2)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 178469707HCID 178469707, compound

Product 1

HCID 178469708HCID 178469708, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-6-(1,2-dihydroxy-propyl)-5,6,7,8-tetrahydro-1H-pteridin-4-one dihydrochloride (1.63 g, 5.2 mmol) was dissolved in 50 mL of pyridine under a nitrogen atmosphere. To this solution was added benzyl chloroformate (1.93 ml, 13.5 mmol). The reaction mixture was degassed under vacuum and placed under an atmosphere of nitrogen. The mixture was stirred for 12 h at room temperature. The solvent was evaporated in vacuo and the residue purified by preparative RP-HPLC to give the sub-titled compound as a white solid (0.93 g, 48% yield). 1H NMR (DMSO-d6) δ 10.02 (s, 1H), 7.41-7.30 (m, 5H), 6.84 (s, 1H), 6.12 (s, 2H), 5.10-4.99 (m, 2H), 3.93 (d, J=6.0 Hz, 1H), 3.66 (dd, J=2.4 Hz, J=6.3 Hz, 1H), 3.56 (dd, J=4.8 Hz, J=12 Hz, 1H), 3.25 (d, J=10.5 Hz, 1H), 3.03 (dd, J=4.5 Hz, J=12.4 Hz, 1H), 1.26 (d, J=6.3 Hz, 1H). MS: ESI (positive): 376 (M+H).

Workup

  1. customThe reaction mixture was degassed under vacuum
  2. customThe solvent was evaporated in vacuo
  3. customthe residue purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-d50a92439f9244b0afcf253d54701191
Source dataset
uspto-grants-2012_12
Patent number
US08324210B2

Reaction notes

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