Ethyl pyruvate → HCID 69658157, compound

HRID 1831598Notes

Reaction equation

HRID 1831598 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]([CH3:21])[CH2:18][O:19][CH3:20])[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]([CH3:21])[CH2:18][O:19][CH3:20])[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 69658135HCID 69658135, compound

Product 1

HCID 69658157HCID 69658157, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

(R)-6-(2-Chloro-4-methoxy-phenyl)-N4-(2-methoxy-1-methyl-ethyl)-pyrimidine-4,5-diamine (0.26 g, 0.82 mmol) was diluted in ethanol (8 ml) and ethyl pyruvate was added (0.92 ml, 8.2 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 6.0 mg of (R)-4-(2-chloro-4-methoxy-phenyl)-8-(2-methoxy-1-methyl-ethyl)-6-methyl-8H-pteridin-7-one (Example 570a). 1H NMR (300 MHz, CDCl3) δ ppm 9.09 (s, 1 H), 7.43 (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), 4.39 (m, 3H), 3.91 (s, 3 H), 3.73 (dd, J=10.07, 5.31 Hz, 2 H), 3.35 (s, 3H), 2.53 (s, 3 H), 1.62 (6, J=6.96 Hz, 3 H). MS (AP) 375.2 [(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-9087bc3683df4a479340426781d05791
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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