Triethylamine → 2,2-Dimethyl-N-(6-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)propanamide

HRID 1842586Notes

Reaction equation

HRID 1842586 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[NH:10][C:9]([CH3:11])=[CH:8][C:6]=2[N:7]=1.[CH3:13][C:14]([CH3:19])([CH3:18])[C:15](Cl)=[O:16].C(N(CC)CC)C.CO.C(Cl)(Cl)Cl>ClC(Cl)C.CN(C1C=CN=CC=1)C.ClCCl>[CH3:13][C:14]([CH3:19])([CH3:18])[C:15]([NH:1][C:2]1[NH:3][C:4](=[O:12])[C:5]2[NH:10][C:9]([CH3:11])=[CH:8][C:6]=2[N:7]=1)=[O:16]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 21584188Chloroform methanolHCID 135797460HCID 135797460, compound

Product 1

HCID 1357974532,2-Dimethyl-N-(6-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)propanamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a 250-mL round-bottomed flask was added 8 (1.37 g, 8 mmol), suspended in 40 mL of dichloroethane; then trimethylacetyl chloride (1.99 mL, 16 mmol), DMAP (0.13 g, 1 mmol) and triethylamine (2.68 mL) were added. The mixture was stirred overnight at 50° C. The resulting mixture was cooled, diluted with dichloromethane (50 mL), washed with brine (40 mL×2), dried over Na2SO4 and concentrated in vacuo. To this solution were added methylene chloride (30 mL) and silica gel (5 g) and the solvent evaporated. The silica gel plug obtained was loaded onto a silica gel column and eluted with 9:1 ethyl acetate/n-hexane The fractions containing the product (TLC) were pooled and the solvent was evaporated to afford 1.33 g (67%) of9 as a white solid: TLC Rf0.47 (MeOH/CHCl3, 1:10); mp 156-157° C.; 1H NMR (DMSO-d6) δ 1.19 (s, 9 H), 2.29 (s, 3 H), 5.97 (s, 1 H), 10.72 (s, 1 H), 11.78 (s, 1 H), 11.87 (s, 1 H). Anal. (C12H16N4O20.15CH3COCH3) C, H, N.

Workup

  1. temperatureThe resulting mixture was cooled
  2. washwashed with brine (40 mL×2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. additionTo this solution were added methylene chloride (30 mL) and silica gel (5 g)
  6. customthe solvent evaporated
  7. customThe silica gel plug obtained
  8. washeluted with 9:1 ethyl acetate/n-hexane The fractions
  9. additioncontaining the product (TLC)
  10. customthe solvent was evaporated
  11. customto afford 1.33 g (67%) of9 as a white solid

Sources & evidence

ORD record
ord-afc43d0c8ed942e2b34f15536b79fa49
Source dataset
uspto-grants-2015_02
Patent number
US08946239B2

Reaction notes

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