Ethyl pyruvate → HCID 69658044, compound

HRID 1831603Notes

Reaction equation

HRID 1831603 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([NH:7][C:8]1[C:13]([NH2:14])=[C:12]([C:15]2[C:16]([CH3:23])=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[N:11]=[CH:10][N:9]=1)[CH2:5][CH3:6].[C:24](OCC)(=[O:28])[C:25]([CH3:27])=O>C(O)C>[CH3:1][O:2][CH2:3][C@H:4]([N:7]1[C:8]2[N:9]=[CH:10][N:11]=[C:12]([C:15]3[C:16]([CH3:23])=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[C:13]=2[N:14]=[C:25]([CH3:27])[C:24]1=[O:28])[CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 69658119HCID 69658119, compound

Product 1

HCID 69658044HCID 69658044, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-N4-(1-Methoxymethyl-propyl)-6-(6-methoxy-2-methyl-pyridin-3-yl)-pyrimidine-4,5-diamine (0.2 g, 0.63 mmol) was diluted in ethanol (7 ml) and ethyl pyruvate was added (0.70 ml, 6.3 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)-8-(1-methoxymethyl-propyl)-4-(6-methoxy-2-methyl-pyridin-3-yl)-6-methyl-8H-pteridin-7-one (Example 651a). 1H NMR (300 MHz, CDCl3) δ ppm 8.93 (s, 1 H), 7.62 (d, J=8.42 Hz, 1 H), 6.64 (d, J=8.42 Hz, 1 H), 4.23 (m, 1H), 3.94 (s, 3 H), 3.68 (m, 2 H), 3.25 (s, 3 H), 2.45 (s, 3H), 2.34 (s, 3 H), 1.22 (m, 2H), 0.82 (t, J=7.51 Hz, 3 H). MS (EI) 370.3 [(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-f6bdb8792045410d8d6971da4e40ee21
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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