P-Anisidine → HCID 46913775, compound

HRID 536026Notes

Reaction equation

HRID 536026 reaction equation
Cl[C:2]1[N:3]([CH2:18][CH2:19][CH3:20])[C:4](=[O:17])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[N:8][C:9]=2[N:10]=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1>C(O)CCC>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:2]2[N:3]([CH2:18][CH2:19][CH3:20])[C:4](=[O:17])[C:5]3[NH:6][C:7]([C:11]4[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=4)=[N:8][C:9]=3[N:10]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 46913776HCID 46913776, compound

Product 1

HCID 46913775HCID 46913775, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of 2-Chloro-8-(1-methyl-1H-pyrazol-4-yl)-1-propyl-1,7-dihydro-purin-6-one (0.1 g, 0.34 mmol), p-anisidine (0.049 g, 0.4 mmol) and 1-butanol (5 ml), were heated at reflux temperature for 20 hours. The reaction mixture was cooled to 20-25° C. and evaporated to dryness, then added water (20 ml) to the residue and extracted with ethyl acetate (4×20 ml). The organic layers were mixed and washed with brine (30 ml), dried over Na2SO4 and evaporated to dryness and the crude product was washed with diethyl ether and dried to obtain 2-(4-Methoxy-phenylamino)-8-(1-methyl-1H-pyrazol-4-yl)-1-propyl-1,7-dihydro-purin-6-one (0.0625 g, 48%) as an off white solid.

Workup

  1. temperaturewere heated
  2. temperatureat reflux temperature for 20 hours
  3. customevaporated to dryness
  4. extractionadded water (20 ml) to the residue and extracted with ethyl acetate (4×20 ml)
  5. additionThe organic layers were mixed
  6. washwashed with brine (30 ml)
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness
  9. washthe crude product was washed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-3f04ad38af234047bf353865e8a289bf
Source dataset
uspto-grants-2014_10
Patent number
US08859566B2

Reaction notes

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