Methyl chloroformate → 2-Methylpentane

HRID 1611031Notes

Reaction equation

HRID 1611031 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]([S:13][C:14]2[C:22]3[C:21](=[O:23])[N:20]([CH3:24])[C:19](=[O:25])[N:18]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]=3[S:16][C:15]=2[CH2:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=[CH:33][CH:32]=2)[CH:10]=[CH:11][CH:12]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:30][CH2:15][CH2:14][CH:22]([CH3:21])[CH3:17].[CH3:5][O:4][C:2]([NH:6][C:7]1[CH:8]=[C:9]([S:13][C:14]2[C:22]3[C:21](=[O:23])[N:20]([CH3:24])[C:19](=[O:25])[N:18]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:17]=3[S:16][C:15]=2[CH2:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=[CH:33][CH:32]=2)[CH:10]=[CH:11][CH:12]=1)=[O:3]

Participants

7

Reactant 4

HCID 6586Methyl chloroformate2×HCID 8471Triethylamine2×HCID 516892Sodium BicarbonateHCID 22258012HCID 22258012, compound

Product 2

HCID 78922-MethylpentaneHCID 22258004HCID 22258004, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chloroformate (0.028 ml) was added to a solution of 5-[(3-aminophenyl)thio]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl) thieno[2,3-d]pyrimidine-2,4-(1H,3H)-dione (60 mg) and triethylamine (0.067 ml) in anhydrous dichloromethane (2 ml) at room temperature. Further triethylamine (0.067 ml) and methyl chloroformate (0.028 ml) were added after 4 hours and 24 hours. Saturated sodium hydrogen carbonate solution (10 ml) was added and the mixture was extracted with ether (2×10 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by preparative normal-phase HPLC with dichloromethane:ethanol gradient elution and then recrystallised from ethyl acetate:isohexane to give the title compound (15 mg).

Workup

  1. extractionthe mixture was extracted with ether (2×10 ml)
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by preparative normal-phase HPLC with dichloromethane
  6. washethanol gradient elution
  7. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-b71ce9d5f6d546cea911efb813238651
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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