Toluene → HCID 59717154, compound

HRID 75639Notes

Reaction equation

HRID 75639 reaction equation
[CH3:1][N:2]1[C:7]2[N:8]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:9](=[O:19])[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11](=[O:12])[C:6]=2[C:5](SC)=[N:4][C:3]1=[O:28].C1(C)C=CC=CC=1.[Cl:36][C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1>C(OCC)C>[Cl:36][C:37]1[CH:43]=[CH:42][C:40]([NH:41][C:5]2[C:6]3[C:11](=[O:12])[N:10]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:9](=[O:19])[N:8]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:7]=3[N:2]([CH3:1])[C:3](=[O:28])[N:4]=2)=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 78124-ChloroanilineHCID 597172888-methyl-5-methylsulfanyl-1,3-diphenyl-1H,8H-pyrimido[4,5-d]pyrimidine-2,4,7-trione

Product 1

HCID 59717154HCID 59717154, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 8-methyl-5-methylsulfanyl-1,3-diphenyl-1H,8H-pyrimido[4,5-d]pyrimidine-2,4,7-trione 26 (149 mg) obtained in Step 6 was added toluene (2 ml), 4-chloroaniline 27 (97 mg) was added, and the mixture was stirred under reflux for 3.5 hrs. After allowing to cool to room temperature, diethyl ether was added. The crystals were collected by filtration, washed with diethyl ether and dried to give 5-(4-chloro-phenylamino)-8-methyl-1,3-diphenyl-1H,8H-pyrimido[4,5-d]pyrimidine-2,4,7-trione 28 (94 mg, yield 53%) as colorless crystals.

Workup

  1. additionwas added
  2. temperatureunder reflux for 3.5 hrs
  3. filtrationThe crystals were collected by filtration
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-e7e44687010140c1b060c0c08bbd4cce
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Reaction notes

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