Ethyl pyruvate → HCID 69658115, compound

HRID 1831602Notes

Reaction equation

HRID 1831602 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([NH:6][C:7]1[C:12]([NH2:13])=[C:11]([C:14]2[C:15]([CH3:22])=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[N:10]=[CH:9][N:8]=1)[CH3:5].[C:23](OCC)(=[O:27])[C:24]([CH3:26])=O>C(O)C>[CH3:1][O:2][CH2:3][C@H:4]([N:6]1[C:7]2[N:8]=[CH:9][N:10]=[C:11]([C:14]3[C:15]([CH3:22])=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[C:12]=2[N:13]=[C:24]([CH3:26])[C:23]1=[O:27])[CH3:5]

Participants

4

Reactant 2

HCID 12041Ethyl pyruvateHCID 69658047HCID 69658047, compound

Product 1

HCID 69658115HCID 69658115, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-N4-(2-Methoxy-1-methyl-ethyl)-6-(6-methoxy-2-methyl-pyridin-3-yl)-pyrimidine-4,5-diamine (0.22 g, 0.74 mmol) was diluted in ethanol (8 ml) and ethyl pyruvate was added (0.82 ml, 7.4 mmol). The mixture was stirred for 18 hours at which time the solution was concentrated. After concentrating the solution the product was purified by preparative TLC eluting with 35% ethyl acetate in hexanes to yield 5.0 mg of (R)-8-(2-methoxy-1-methyl-ethyl)-4-(6-methoxy-2-methyl-pyridin-3-yl)-6-methyl-8H-pteridin-7-one (Example 650a). 1H NMR (300 MHz, CDCl3) δ ppm 8.99 (s, 1 H), 7.65 (d, J=8.42 Hz, 1 H), 6.68 (d, J=8.42 Hz, 1 H), 5.71 (m, 1H), 3.99 (s, 3 H), 3.59 (m, 2 H), 3.31 (s, 3 H), 2.50 (s, 3H), 2.50 (s, 3H), 2.50 (s, 3H), 0.85 (d, J=7.69 Hz, 3 H). MS (EI) 356.3 [(M+H)+, 100].

Workup

  1. concentrationwas concentrated
  2. concentrationAfter concentrating the solution the product
  3. customwas purified by preparative TLC
  4. washeluting with 35% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6fbfeb54ac3a4af19a873fc5d846e95a
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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