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Ethanol → 2-(3-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 2428011
Notes
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Reaction equation

HRID 2428011 reaction equation
[NH2:1][C:2]1[C:3]([C:26](OCC)=[O:27])=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][OH:25])[CH:19]=2)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16].OC1C=CC=CC=1[N:38](CC)N1C(C([O-])=O)=CC(NC2C=CC=CC=2OC)=NC1.[CH2:59]([OH:61])C>[Pd]>[OH:25][CH2:24][C:20]1[CH:19]=[C:18]([NH:17][C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:59](=[O:61])[N:8]3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:3]([C:26]([NH2:38])=[O:27])[N:4]=2)[CH:23]=[CH:22][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 57474710Ethyl 5-amino-2-(3-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylateHCID 178463277HCID 178463277, compound

Product 1

HCID 574747082-(3-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 23938
Palladium
Catalyst

Procedure

Ethyl 5-amino-2-(3-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl-5-nitro-2-(3-(hydroxy(ethyl)phenylamino)-6-(2-methoxy-phenylamino)pyrimidine-4-carboxylate (0.35 g, 0.797 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.087 g) was added to the flask and flushed with fresh hydrogen gas and allowed to stir at room temperature. After 16 h, the reaction was filtered through celite and the filtrate condensed under reduced pressure. The crude oil was purified using biotage chromatography (50-100% ethyl acetate in hexanes) to afford the title compound (0.277 g, 85%). MS (ESI) m/z 410.5 [M+1]+.

Workup

  1. customflushed with fresh hydrogen gas
  2. filtrationthe reaction was filtered through celite
  3. customthe filtrate condensed under reduced pressure
  4. customThe crude oil was purified

Sources & evidence

ORD record
ord-abe7810b681541fab466d5afcd67aad7
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968556B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes