Ethyl Acetate → HCID 59834698, compound

HRID 271552Notes

Reaction equation

HRID 271552 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][OH:16].[H-].[Na+].[Cl:21][C:22]1[CH:27]=[C:26](Cl)[N:25]=[CH:24][N:23]=1.CCOC(C)=O>C1COCC1.O.CCCCCC>[Cl:21][C:22]1[N:23]=[CH:24][N:25]=[C:26]([O:16][CH2:15][C:5]2[N:4]([CH2:3][C:2]([CH3:18])([CH3:17])[CH3:1])[C:8]3[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=3[CH:6]=2)[CH:27]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 59834672HCID 59834672, compound

Product 1

HCID 59834698HCID 59834698, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 7-(2,2-dimethyl-propyl)-6-hydroxymethyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (1.0 mmol) in THF (10 ml) is added NaH (1.2 mmol) at room temperature under nitrogen atmosphere. After 15 min stirring, 4,6-dichloropyrimidine (1.1 mmol) is added and the mixture is stirred at room temperature for 1 h. The reaction mixture is diluted with H2O and extracted with AcOEt. The organic extracts are dried over Na2SO4 and concentrated. The residue obtained is purified by column chromatography on silica gel to give the product in 92% yield. Rf=0.49 (AcOEt:n-hexane=1:2). 1H NMR(400 MHz, CDCl3) δ 1.05 (s, 9H), 4.26(s, 2H), 5.74(s, 2H), 6.83(s, 1H), 6.86(s, 1H), 8.62(s, 1H), 8.97(s, 1H).

Workup

  1. stirringthe mixture is stirred at room temperature for 1 h
  2. extractionextracted with AcOEt
  3. dry with materialThe organic extracts are dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customis purified by column chromatography on silica gel
  7. customto give the product in 92% yield

Sources & evidence

ORD record
ord-7441487a13f1448497a9db43b5fc4202
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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