Ethyl pyruvate → HCID 69658149, compound

HRID 1831601Notes

Reaction equation

HRID 1831601 reaction equation
[CH:1]1([C@H:4]([NH:7][C:8]2[C:13]([NH2:14])=[C:12]([C:15]3[C:16]([CH3:23])=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[N:11]=[CH:10][N:9]=2)[CH2:5][CH3:6])[CH2:3][CH2:2]1.[C:24](OCC)(=[O:28])[C:25]([CH3:27])=O>C(O)C>[CH:1]1([C@H:4]([N:7]2[C:8]3[N:9]=[CH:10][N:11]=[C:12]([C:15]4[C:16]([CH3:23])=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=4)[C:13]=3[N:14]=[C:25]([CH3:27])[C:24]2=[O:28])[CH2:5][CH3:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 69657972HCID 69657972, compound

Product 1

HCID 69658149HCID 69658149, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-N4-(1-Cyclopropyl-propyl)-6-(6-methoxy-2-methyl-pyridin-3-yl)-pyrimidine-4,5-diamine (0.20 g, 0.64 mmol) was diluted in ethanol (7 ml) and ethyl pyruvate was added (0.73 ml, 6.4 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 2.0 mg of (R)-8-(1-cyclopropyl-propyl)-4-(6-methoxy-2-methyl-pyridin-3-yl)-6-methyl-8H-pteridin-7-one (Example 644a). 1H NMR (300 MHz, CDCl3) δ ppm 8.92 (s, 1 H), 7.68 (d, J=8.05 Hz, 1 H), 6.68 (d, J=9.15 Hz, 1 H), 4.84 (m, 1 H), 3.99 (s, 3 H),), 2.51 (s, 3 H), 2.39 (s, 3 H), 1.20 (m, 2 H), 0.86 (m, 8 H). MS (EI) 366.3 [(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-e3f894bf51ba4d488032d4d2dc2f7cd0
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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