Diethyl Oxalate → 8-Cyclopentyl-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-5H,8H-pteridine-6,7-dione

HRID 1375419Notes

Reaction equation

HRID 1375419 reaction equation
[NH2:1][C:2]1[C:3]([NH:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[C:28](OCC)(=[O:34])[C:29](OCC)=[O:30]>C(OCCO)C>[CH:23]1([N:22]2[C:3]3[N:4]=[C:5]([NH:8][C:9]4[CH:14]=[CH:13][C:12]([N:15]5[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]5)=[CH:11][CH:10]=4)[N:6]=[CH:7][C:2]=3[NH:1][C:29](=[O:30])[C:28]2=[O:34])[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 587868155-Amino-4-(cyclopentylamino)-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]pyrimidine

Product 1

HCID 98235148-Cyclopentyl-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-5H,8H-pteridine-6,7-dioneYield 52.2%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 0.367 g (1 mmol) of 5-amino-4-(cyclopentylamino)-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]pyrimidine and 5 mL (32 mmol) of diethyl oxalate in 20 mL of 2-ethoxyethanol is heated under reflux for 3 hours, and cooled, to give 0.22 g (52%) of the title compound (Compound 24): mp (EtOH) 266–270° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled

Sources & evidence

ORD record
ord-0b07a8ac0499467183526f450cebb74c
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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