Ethyl pyruvate → HCID 10317762, compound

HRID 1831604Notes

Reaction equation

HRID 1831604 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][C@@H:17]([CH2:20][O:21][CH3:22])[CH2:18][CH3:19])[C:11]=2[NH2:23])=[C:5]([CH3:24])[CH:4]=1.[C:25](OCC)(=[O:29])[C:26]([CH3:28])=O>C(O)C>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]2[C:11]3[N:23]=[C:26]([CH3:28])[C:25](=[O:29])[N:16]([C@@H:17]([CH2:20][O:21][CH3:22])[CH2:18][CH3:19])[C:12]=3[N:13]=[CH:14][N:15]=2)=[C:5]([CH3:24])[CH:4]=1

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 69658311HCID 69658311, compound

Product 1

HCID 10317762HCID 10317762, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-6-(4-Methoxy-2,5-dimethyl-phenyl)-N4-(1-methoxymethyl-propyl)-pyrimidine-4,5-diamine (0.22 g, 0.68 mmol) was diluted in ethanol (7 ml) and ethyl pyruvate was added (0.76 ml, 6.8 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 8.0 mg of (R)-4-(4-methoxy-2,5-dimethyl-phenyl)-8-(1-methoxymethyl-propyl)-6-methyl-8H-pteridin-7-one (Example 1013a). 1H NMR (300 MHz, CDCl3) δ ppm 9.05 (s, 1 H), 7.21 (s, 1 H), 6.79 (s, 1 H), 4.86 (m, 1 H), 3.91 (s, 3 H), 2.55 (m, 3 H), 2.38 (m, 1 H), 2.22 (s, 3 H),), 2.22 (s, 3 H), 2.04 (m, 1 H), 1.25 (m, 1 H), 0.89 (t, J=7.51 Hz, 3 H), 0.77 (m, 1 H), 0.50 (m, 1 H), 0.39 (m, 1 H), 0.18 (m, 1 H). MS (EI) 379.3 [(M+H)+, 100].

Workup

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

Sources & evidence

ORD record
ord-40f37bbc75fa4a8d9ae58aa65585b7f1
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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