Ethyl pyruvate → HCID 10432748, compound

HRID 1831606Notes

Reaction equation

HRID 1831606 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[C:13]1[N:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([CH3:24])[CH2:21][O:22][CH3:23])[C:14]=1[NH2:25].[C:26](OCC)(=[O:30])[C:27]([CH3:29])=O>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:10])([F:12])[F:11])[CH:5]=[CH:4][C:3]=1[C:13]1[C:14]2[N:25]=[C:27]([CH3:29])[C:26](=[O:30])[N:19]([C@H:20]([CH3:24])[CH2:21][O:22][CH3:23])[C:15]=2[N:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 69658130HCID 69658130, compound

Product 1

HCID 10432748HCID 10432748, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-6-(2-Chloro-4-trifluoromethoxy-phenyl)-N4-(2-methoxy-1-methyl-ethyl)-pyrimidine-4,5-diamine (0.20 g, 0.53 mmol) was diluted in ethanol (6 ml) and ethyl pyruvate was added (0.59 ml, 5.3 mmol). The mixture was stirred for 18 hours at which time the solution was concentrated. After concentrating the solution the product was purified by reverse phase HPLC to yield 4.0 mg of (R)-4-(2-chloro-4-trifluoromethoxy-phenyl)-8-(2-methoxy-1-methyl-ethyl)-6-methyl-8H-pteridin-7-one (Example 1067a). 1H NMR (300 MHz, CDCl3) δ ppm 9.02 (s, 1 H), 7.49 (d, J=8.42 Hz, 1 H), 7.39 (d, J=1.10 Hz, 1 H), 7.26 (dd, J=8.42, 1.10 Hz, 1 H), 5.95 (s, 1 H), 4.36 (t, J=9.52 Hz, 1 H), 3.68 (dd, J=10.07, 5.31 Hz, 1 H), 3.30 (s, 3 H), 2.48 (s, 3 H), 1.58 (d, J=6.96 Hz, 3 H).

Workup

  1. concentrationwas concentrated
  2. concentrationAfter concentrating the solution the product
  3. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-980138fcb6b84be084dfc7621520bfce
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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