Dimethylformamide → HCID 58180959, compound

HRID 1772818Notes

Reaction equation

HRID 1772818 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1.CN(C)C=O.[H-].[Na+].Br[CH:31]([CH2:37][CH3:38])[C:32]([O:34][CH2:35][CH3:36])=[O:33]>O.C(OCC)(=O)C>[CH3:20][Si:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][O:16][CH2:15][N:12]1[C:8]2[N:9]=[CH:10][N:11]=[C:6]([C:4]3[CH:5]=[N:1][N:2]([CH:31]([CH2:37][CH3:38])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:3]=3)[C:7]=2[CH:14]=[CH:13]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 426313464-(1H-Pyrazol-4-yl)-7-(2-(trimethylsilyl)ethoxy)methyl-7 H-pyrrolo(2,3-d)-pyrimidine

Product 1

HCID 58180959HCID 58180959, compoundYield 111.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 4-(1H-pyrazol-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (2.0 g, 0.0063 mol) in N,N-dimethylformamide (40 mL, 0.5 mol) was added sodium hydride (0.30 g, 0.0076 mol). After 15 minutes, ethyl 2-bromobutyrate (1.4 mL, 0.0095 mol) was added. After 4.5 hours, ethyl acetate and water were added. The organic phase was washed with water twice and saturated NaCl. The organic phase was then and the solvent was removed by rotary evaporation to give 3.02 g of a thick orange oil (110% yield). 1H NMR (400 MHz, CDCl3): δ 8.92 (1H, s); 8.49 (1H, s); 8.35 (1H, s); 7.45 (1H, d); 6.85 (1H, d); 6.75 (2H, s); 5.0 (1H, t); 4.35 (2H, m); 3.6 (2H, t); 2.35 (2H, m); 1.35 (6H, m); (1.0 (3H, m); 0 (9H, s). LCMS (M+1): 430.

Workup

  1. waitAfter 4.5 hours
  2. washThe organic phase was washed with water twice
  3. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-84ba985a99e44010bf8d64aef61a0200
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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