1-Bromopropane → HCID 59519291, compound

HRID 237378Notes

Reaction equation

HRID 237378 reaction equation
Br[CH2:2][CH2:3][CH3:4].[CH2:5]([O:7][C:8]([C:10]1[S:27][C:13]2[N:14]=[C:15]([NH2:26])[N:16]=[C:17]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:19]=3[CH3:25])[C:12]=2[CH:11]=1)=[O:9])[CH3:6].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:5]([O:7][C:8]([C:10]1[S:27][C:13]2[N:14]=[C:15]([NH2:26])[N:16]=[C:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:2][CH2:3][CH3:4])=[CH:20][C:19]=3[CH3:25])[C:12]=2[CH:11]=1)=[O:9])[CH3:6]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 136174006HCID 136174006, compound

Product 1

HCID 59519291HCID 59519291, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1-Bromopropane (15 uL; 0.17 mmol) was added to a solution of 2-Amino-4-(4-hydroxy-2-methyl-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (50 mg: 0.152 mmol) and potassium carbonate (25 mg; 0.18 mmol) in DMF (15 mL). Reaction mixture was heated to 50 degrees C. for 18 hours. Reaction mixture was allowed to cool and solvent removed in vacuo. Residue was partitioned between saturated aqueous sodium bicarbonate solution (10 mL) and ethyl acetate (20 mL). Organic phase was dried over Na2SO4 and filtered, filtrate solvents removed in vacuo to afford a yellow solid purified by flash chromatography on silica gel (eluting ethyl acetate in hexane) to afford product as yellow solid (45 mg; 80%)

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. temperatureto cool
  4. customsolvent removed in vacuo
  5. customResidue was partitioned between saturated aqueous sodium bicarbonate solution (10 mL) and ethyl acetate (20 mL)
  6. dry with materialOrganic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customfiltrate solvents removed in vacuo
  9. customto afford a yellow solid
  10. custompurified by flash chromatography on silica gel (eluting ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1dc9d42f21ec43248e39bb152c312af8
Source dataset
uspto-grants-2014_02
Patent number
US08642594B2

Reaction notes

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