Ammonia → HCID 57474695, compound

HRID 2428009Notes

Reaction equation

HRID 2428009 reaction equation
C(OC(C1N=C(NCCO)N=C2C=1NC(=O)N2C1C=CC=CC=1OC)=O)C.[OH:28][CH2:29][CH2:30][NH:31][C:32]1[N:40]=[C:39]2[C:35]([NH:36][C:37](=[O:49])[N:38]2[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:47][CH3:48])=[C:34]([C:50]([NH2:52])=[O:51])[N:33]=1.N>CO>[OH:28][CH2:29][CH2:30][NH:31][C:32]1[N:40]=[C:39]2[C:35]([NH:36][C:37](=[O:49])[N:38]2[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:47][CH3:48])=[C:34]([C:50]([NH2:52])=[O:51])[N:33]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67148035HCID 67148035, compound

Product 1

HCID 57474695HCID 57474695, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2-Hydroxyethylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide Ethyl 2-(2-hydroxyethylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxylate (0.400 g) and ammonia gas in methanol (10 mL) were reacted according to General Procedure G and purified using reverse-phase preparative HPLC (5-60% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min) to afford the title compound (0.015 g, 8%). 1H NMR (400 MHz, DMSO-d6) δ 10.49 (s, 1H), 7.86 (s, 1H), 7.81 (s, 1H), 7.48 (t, J=6.79, 1H), 7.36 (d, J=7.99, 1H), 7.20 (d, J=8.39, 1H), 7.07 (t, J=7.59, 1H), 6.78 (s, 1H), 4.50 (t, J=5.59, 1H), 3.72 (s, 3H), 3.44 (q, J=6.39, 2H), 3.31 (m, 2H); MS (ESI) m/z 345.2 [M+1]+; mp 157-160° C.

Workup

  1. custompurified
  2. customreverse-phase preparative HPLC (5-60% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)

Sources & evidence

ORD record
ord-dd82f78339e64708a7c01107da97c315
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

Loading…