Ethyl pyruvate → HCID 69658030, compound

HRID 1831597Notes

Reaction equation

HRID 1831597 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][C@H:17]([CH:19]2[CH2:22][CH2:21][CH2:20]2)[CH3:18])[C:11]=1[NH2:23].[C:24](OCC)(=[O:28])[C:25]([CH3:27])=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:23]=[C:25]([CH3:27])[C:24](=[O:28])[N:16]([C@H:17]([CH:19]3[CH2:20][CH2:21][CH2:22]3)[CH3:18])[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 69658242HCID 69658242, compound

Product 1

HCID 69658030HCID 69658030, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

(S)-6-(2-Chloro-4-methoxy-phenyl)-N4-(1-cyclobutyl-ethyl)-pyrimidine-4,5-diamine (0.23 g, 0.69 mmol) was diluted in ethanol (7 ml) and ethyl pyruvate was added (0.78 ml, 6.9 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 2.0 mg of (S)-4-(2-chloro-4-methoxy-phenyl)-8-(1-cyclobutyl-ethyl)-6-methyl-8H-pteridin-7-one (Example 567a). 1H NMR (300 MHz, CDCl3) δ ppm 9.06 (s, 1 H), 7.46 (d, J=8.79 Hz, 1 H), 7.09 (d, J=2.56 Hz, 1 H), 6.97 (dd, J=8.79, 2.56 Hz, 1 H), 5.82 (m, 1 H), 3.91 (s, 3 H), 2.51 (s, 3 H), 2.22 (m, 2 H), 1.87 (m, 4 H), 1.74 (s, 3 H), 1.55 (m, 1 H). MS (AP) 385.3 [(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-a1e572f14afb4f30acec2278516e3947
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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