HCID 14267830, compound → HCID 70360267, compound

HRID 1650895Notes

Reaction equation

HRID 1650895 reaction equation
C(OCC1C=N[C:9]2[NH:10][C:11](=[O:15])[NH:12][C:13](=[O:14])[C:8]=2[C:7]=1[CH2:18][NH:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[O:28][CH3:29])(=O)C>C1(OC2C=CC=CC=2)C=CC=CC=1.C(O)C.C(OCC)C>[CH3:29][O:28][C:21]1[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:20]=1[N:19]1[CH2:9][C:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10][C:7]=2[CH2:18]1

Participants

5

Reactant 1

HCID 14267830HCID 14267830, compound

Product 1

HCID 70360267HCID 70360267, compoundYield 107.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 7583Diphenyl EtherSolvent

Procedure

6-Acetoxymethyl-5-(2,5-dimethoxyanilino)methylpyrido[2,3-d]-pyrimidine-2,4(1H,3H)-dione (400 mg, 1 mmol) in diphenyl ether is heated at 210° C. for 2 hours under nitrogen. The resulting clear solution is cooled and then is diluted with a 1:1 mixture of ethanol and diethyl ether (100 mL). The yellow precipitate is collected by filtration and is washed with boiling mixture of chloroform and ethanol (1:1 v/v) to give 6-(2,5-dimethoxyphenyl)-6,7-dihydropyrrolo[3,4-d]pyrimidine-2,4(1H,3H)-dione (311 mg, 91%), mp 308°-310° C. 1H NMR (Me2SO-d6) d 3.70 (3H, s, OMe), 3.74 (3H, s, OMe), 4.67 (2H, brs, CH2), 4.98 (2H, brs, CH2), 6.28 (1H, s, H-6'), 6.31 and 6.87 (each 1H, d, H-3' and H-4' ), 8.53 (1H, s, H-2), 11.43 and 11.61 (each 1H, brs, NH, exchangeable).

Workup

  1. temperatureThe resulting clear solution is cooled
  2. filtrationThe yellow precipitate is collected by filtration
  3. washis washed
  4. additionmixture of chloroform and ethanol (1:1 v/v)

Sources & evidence

ORD record
ord-21481d37bdb94b0c8966d5a1a7a018e7
Source dataset
uspto-grants-1990_05
Patent number
US04925939

Reaction notes

Loading…