Dimethylformamide dimethyl acetal → HCID 68032343, compound

HRID 1397172Notes

Reaction equation

HRID 1397172 reaction equation
[C:1]([C:4]1[C:5]([CH3:11])=[N:6][C:7]([NH2:10])=[N:8][CH:9]=1)(=[O:3])[CH3:2].[CH3:12][N:13]([CH:15](OC)OC)[CH3:14]>>[CH3:12][N:13]([CH3:15])/[CH:14]=[CH:2]/[C:1]([C:4]1[C:5]([CH3:11])=[N:6][C:7]([N:10]=[CH:12][N:13]([CH3:15])[CH3:14])=[N:8][CH:9]=1)=[O:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 4598125-Acetyl-2-amino-4-methylpyrimidine

Product 1

HCID 68032343HCID 68032343, compoundYield 61%

Procedure

A solution of 5-acetyl-2-Amino-4-methypyrimidine (Alfa Aesar) (1.00 g, 6.62 mmol) in DMF-DMA (35.4 mL, 265 mmol) was heated at 120° C. for 18 hours. The reaction mixture was concentrated in vacuo, then was purified by Biotage™ silica gel chromatography [50 g SNAP column, 2-10% MeOH/DCM] to obtain a pale yellow solid as the desired product, which was dried over high vacuum for 1 hour (1.06 g, 61% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.42 (s, 3 H) 2.86 (br. s., 3 H) 3.03 (s, 3 H) 3.10 (br. s., 3 H) 3.13 (s, 3 H) 5.40 (d, J=12.63 Hz, 1 H) 7.50 (d, J=12.63 Hz, 1 H) 8.48 (s, 1 H) 8.64 (s, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customwas purified by Biotage™ silica gel chromatography [50 g SNAP column, 2-10% MeOH/DCM]

Sources & evidence

ORD record
ord-e693515840fb41e19524f799070b8587
Source dataset
uspto-grants-2014_12
Patent number
US08901147B2

Reaction notes

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