Acetic Acid → HCID 69732875, compound

HRID 2416425Notes

Reaction equation

HRID 2416425 reaction equation
[CH2:1]([N:8]1[C:13]2[N:14]([CH3:27])[C:15](=[O:26])[N:16]([CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([OH:25])[CH3:24])[C:17](=[O:18])[C:12]=2[C:11](=[O:28])[CH:10]=[C:9]1[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:49](O)(=[O:51])[CH3:50].CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:49]([O:25][C@@H:23]([CH3:24])[CH2:22][CH2:21][CH2:20][CH2:19][N:16]1[C:17](=[O:18])[C:12]2[C:11](=[O:28])[CH:10]=[C:9]([CH3:29])[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:13]=2[N:14]([CH3:27])[C:15]1=[O:26])(=[O:51])[CH3:50]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 60123474HCID 60123474, compound

Product 1

HCID 69732875HCID 69732875, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (R)-8-benzyl-1,7-dimethyl-3-(5-hydroxyhexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.26 g, 3.18 mmol), triphenylphosphine (2.50 g, 9.52 mmol), acetic acid (0.54 ml, 9.52 mmol) and tetrahydrofuran (20 ml), cooled in an ice bath, was added diethylazodicarboxylate (1.5 ml, 9.5 mmol) dropwise. After stirring at room temperature for 4hours, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-hexanes to afford (S)-3-(5-acetoxyhexyl)-8-benzyl-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.2 g, 86% yield) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.20 (d, 3H), 1.30-1.75 (m, 6H), 2.02 (s, 3H), 2.49 (s, 3H), 3.67 (s, 3H), 4.03 (t, 2H), 4.88 (sextet, 1H), 5.30 (s, 2H), 6.56 (s, 1H), 7.30-7.56 (m, 5H).

Workup

  1. temperaturecooled in an ice bath
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-283ccd95c09246eda992ed412020edda
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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