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

HRID 391681Notes

Reaction equation

HRID 391681 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]=[CH:20][C:19]=2[CH2:24][OH:25])=[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].C(OC(C1C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=C(NC2C=CC=CC=2CO)[N:37]=1)=O)C.[CH2:63]([OH:65])C>[Pd]>[OH:25][CH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:5]1[N:6]=[C:7]2[C:2]([NH:1][C:63](=[O:65])[N:8]2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:3]([C:26]([NH2:37])=[O:27])[N:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 57474717HCID 57474717, compoundHCID 57474718Ethyl 5-amino-2-(2-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

Product 1

HCID 574747162-(2-(Hydroxymethyl)phenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideYield 89%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Ethyl 5-amino-2-(2-(hydroxymethyl)phenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl-5-nitro-2-(2-(hydroxymethyl)phenylamino)-6-(2-methoxy-phenylamino)pyrimidine-4-carboxylate (0.325 g, 0.740 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.081 g) were 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 (0.270 g., 89%). 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-c3167033df1c4c5a95e51ed9350c1e65
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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