Ethyl pyruvate → HCID 10022092, compound

HRID 1831596Notes

Reaction equation

HRID 1831596 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[CH2:21][CH2:20]2)[CH3:18])[C:11]=1[NH2:22].[C:23](OCC)(=[O:27])[C:24]([CH3:26])=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:22]=[C:24]([CH3:26])[C:23](=[O:27])[N:16]([C@@H:17]([CH:19]3[CH2:20][CH2:21]3)[CH3:18])[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 69658167HCID 69658167, compound

Product 1

HCID 10022092HCID 10022092, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

(R)-6-(2-Chloro-4-methoxy-phenyl)-N4-(1-cyclopropyl-ethyl)-pyrimidine-4,5-diamine (0.20 g, 0.52 mmol) was diluted in ethanol (5 ml) and ethyl pyruvate was added (0.58 ml, 5.2 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 (R)-4-(2-chloro-4-methoxy-phenyl)-8-(1-cyclopropyl-ethyl)-6-methyl-8H-pteridin-7-one (Example 565a). 1H NMR (300 MHz, CDCl3) δ ppm 9.04 (s, 1 H), 7.45 (d, J=8.42 Hz, 1 H), 7.09 (d, J=2.56 Hz, 1 H), 6.98 (dd, J=8.42, 2.56 Hz, 1 H), 4.26 (m, 1 H), 3.91 (s, 3 H), 2.54 (d, J=7.32, 3 H), 2.18 (m, 3 H), 0.87 (m, 2 H), 0.45 (m, 2 H), 0.26 (m, 1 H). MS (AP) 371.3 [(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-14d4067f353141c9871820933f0c57f8
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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