Triethylamine → HCID 68526687, compound

HRID 1989804Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]([C:11]([NH:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)=[O:12])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=O)[N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Cl)=[CH:37][CH:36]=1>CC(N(C)C)=O.C(OCC)(=O)C>[NH2:1][C:2]1[N:10]=[C:9]([C:11]([NH:13][CH2:14][CH:15]2[CH2:16][CH2:17]2)=[O:12])[N:8]=[C:7]2[C:3]=1[NH:4][CH:5]([CH2:39][C:38]1[CH:41]=[CH:42][C:35]([O:34][CH3:33])=[CH:36][CH:37]=1)[N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 55 °C

Procedure

6-Amino-9-benzyl-N-(cyclopropylmethyl)-8-oxo-8,9-dihydro-7H-purine-2-carboxamide (Example 1, 50 mg, 0.15 mmol) was taken up in 3 ml DMA and firstly triethylamine (27 μl, 0.18 mmol) and then para-methoxybenzyl chloride (26 μl, 0.18 mmol) were added in one portion each and the whole stirred and heated to 55° C. for 16 h. The mixture was diluted with ethyl acetate (5 ml) and washed with water (2×3 ml). The combined organics were dried over MgSO4 and concentrated in vacuo to a yellow residue which was purified by column chromatography using a gradient of 100% DCM:→98:2 DCM:MeOH as the eluant. Combination and evaporation of the appropriate fractions provided the title compound as a white solid (19 mg).

Workup

washwashed with water (2×3 ml)
dry with materialThe combined organics were dried over MgSO4
concentrationconcentrated in vacuo to a yellow residue which
customwas purified by column chromatography
customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record: ord-130a0fc339f5437999daeedb509d2e05
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642350B2

Reaction notes

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