Ethyl pyruvate → HCID 10473966, compound

HRID 1831600Notes

Reaction equation

HRID 1831600 reaction equation
[CH:1]1([C@H:4]([NH:7][C:8]2[C:13]([NH2:14])=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=3[CH3:23])[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[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=4[CH3:23])[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 69658336HCID 69658336, compound

Product 1

HCID 10473966HCID 10473966, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-N4-(1-Cyclopropyl-propyl)-6-(4-methoxy-2-methyl-phenyl)-pyrimidine-4,5-diamine (0.21 g, 0.67 mmol) was diluted in ethanol (7 ml) and ethyl pyruvate was added (0.75 ml, 6.7 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-(4-methoxy-2-methyl-phenyl)-6-methyl-8H-pteridin-7-one (Example 612a). 1H NMR (300 MHz, CDCl3) δ ppm 8.86 (s, 1 H), 7.33 (d, J=9.15 Hz, 1 H), 6.80 (d, J=2.20 Hz, 1 H), 6.78 (d, J=2.20 Hz, 1 H), 4.56 (m, 1 H), 3.80 (s, 3 H), 2.45 (s, 3 H), 2.30 (m, 1 H), 2.20 (s, 3 H), 2.12 (m, 1 H), 0.81 (t, J=7.51 Hz, 3 H), 0.76 (m, 1 H), 0.68 (m, 1 H), 0.42 (m, 1 H), 0.29 (m, 1 H), 0.12 (m, 1 H). MS (EI) 377.3 [(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-a53456c7f15a41c9bde17012c647bebf
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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