Diethyl Oxalate → HCID 9844340, compound

HRID 1375418Notes

Reaction equation

HRID 1375418 reaction equation
[NH2:1][C:2]1[C:3]([NH:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[C:27](OCC)(=[O:33])[C:28](OCC)=[O:29]>C(OCCO)C>[CH:22]1([N:21]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][O:18][CH2:19][CH2:20]5)=[CH:11][CH:10]=4)[N:6]=[CH:7][C:2]=3[NH:1][C:28](=[O:29])[C:27]2=[O:33])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 58786809HCID 58786809, compound

Product 1

HCID 9844340HCID 9844340, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 0.354 g (1 mmol) of 5-amino-4-(cyclopentylamino)-2-[[4-(morpholin-4-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 then cooled to give 0.20 g (49%) of the title compound (Compound 23): mp (EtOH) 283–286° C. 1H NMR [(CD3)2SO]: δ 11.87 (br, 1H, exchangeable with D2O, H-5), 9.29 (br, 1H, exchangeable with D2O, 2NH), 8.12 (s, 1H, H-4), 7.50 (br d, J=9.0 Hz, 2H, H-2′,6′), 6.90 (d, J=9.1 Hz, 2H, H-3′,5′), 5.62 (pentet, J=8.8 Hz, 1H cyclopentyl CH), 3.74 (br t, J=4.7 Hz, 4H, CH2O)), 3.03 (br t, J=4.7 Hz, 4H, CH2N), 2.21–2.11 (m, 2H, cyclopentyl), 1.97–1.84 (m, 2H, cyclopentyl), 1.84–1.74 (m, 2H, cyclopentyl), 1.63–1.52 (m, 2H, cyclopentyl).

Workup

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

Sources & evidence

ORD record
ord-3df28aa21d544cb8acfa64ee42fbfc80
Source dataset
uspto-grants-2007_01
Patent number
US07169778B2

Reaction notes

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