Methyl chloroformate → HCID 69288561, compound

HRID 1766060Notes

Reaction equation

HRID 1766060 reaction equation
[C:1]([NH:5][C:6]([C:8]1[S:25][C:11]2[N:12]=[C:13]([S:23][CH3:24])[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[C:10]=2[C:9]=1[NH2:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl[C:37]([O:39][CH3:40])=[O:38]>C(Cl)Cl>[C:1]([NH:5][C:6]([C:8]1[S:25][C:11]2[N:12]=[C:13]([S:23][CH3:24])[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:37]([O:39][CH3:40])=[O:38])[CH:17]=3)[C:10]=2[C:9]=1[NH2:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 11531195HCID 11531195, compound

Product 1

HCID 69288561HCID 69288561, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 5-amino-2-methylthio-4-(3-hydroxyphenyl)-thieno[2,3-d]pyrimidine-6-carboxamide (example 1f, 100 mg) was dissolved in dry CH2Cl2 (5 ml). DIPEA (500 μl ) and methyl chloroformate (199 μl ) were added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was washed with H2O. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by HPLC using a Luna C-18 column with the following gradient: CH3CN/H2O=10/90 to 90/10 (v/v) in 30 min. The title compound was then lyophilized from a mixture of 1,4-dioxane and H2O.

Workup

  1. washThe reaction mixture was washed with H2O
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe title compound was purified by HPLC
  5. waitCH3CN/H2O=10/90 to 90/10 (v/v) in 30 min
  6. additionThe title compound was then lyophilized from a mixture of 1,4-dioxane and H2O

Sources & evidence

ORD record
ord-0b17191c13f04d329ba3cdcc398a91d4
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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