P-Anisidine → HCID 46913775, compound

HRID 925573Notes

Reaction equation

HRID 925573 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-87e631f78f9d44e1b09c73c51c5e2379
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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