Ethyl pyruvate → HCID 11741745, compound

HRID 1831595Notes

Reaction equation

HRID 1831595 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[C:11]=1[NH2:24].[C:25](OCC)(=[O:29])[C:26]([CH3:28])=O>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[C:11]2[N:24]=[C:26]([CH3:28])[C:25](=[O:29])[N:16]([CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 22052196HCID 22052196, compound

Product 1

HCID 11741745HCID 11741745, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

6-(2-Chloro-4-methoxy-phenyl)-N4-(1-propyl-butyl)-pyrimidine-4,5-diamine (0.29 g, 0.83 mmol) was diluted in ethanol (8 ml) and ethyl pyruvate was added (0.92 ml, 8.3 mmol). The mixture was stirred for 18 hours at which time the solution was concentrated. The residue was diluted in glacial acetic acid (10 ml) and warmed to 100° C. for 1 hour. After concentrating the solution the product was purified by reverse phase HPLC to yield 13.5 mg of 4-(2-chloro-4-methoxy-phenyl)-6-methyl-8-(1-propyl-butyl)-8H-pteridin-7-one (Example 563). 1H NMR (300 MHz, CDCl3) δ ppm 9.02 (s, 1 H), 7.41 (d, J=8.42 Hz, 1 H), 7.05 (d, J=2.56 Hz, 1 H), 6.93 (dd, J=8.42, 2.56 Hz, 1 H), 3.86 (s, 3 H), 4.40 (m, 1H), 2.48 (m, 2 H), 2.31 (m, 2 H), 1.89 (m, 2 H), 1.19 (m, 5 H), 0.88 (t, J=7.32 Hz, 6 H). MS (AP) 321.2 [(M+H)+, 100]. MS (AP) 401.3 [(M+H)+, 100].

Workup

  1. concentrationwas concentrated
  2. additionThe residue was diluted in glacial acetic acid (10 ml)
  3. concentrationAfter concentrating the solution the product
  4. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-4f8739aacf544758b419cc7ae2debace
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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