Diisopropylcarbodiimide → HCID 178473461, compound

HRID 968234Notes

Reaction equation

HRID 968234 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[C:13]([NH2:19])[N:12]=1.[CH2:20]([O:22][C:23]([N:25]=[C:26]=S)=[O:24])[CH3:21].C(N=C=NC(C)C)(C)C>C(#N)C.C(N(CC)CC)C>[NH2:19][C:13]1[N:12]=[C:11]([S:10][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[N:16]=[C:15]2[C:14]=1[N:18]=[C:26]([NH:25][C:23](=[O:24])[O:22][CH2:20][CH3:21])[NH:17]2

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 85320Ethyl isothiocyanatoformateHCID 222885032-[[(2,3-Difluorophenyl)methyl]thio]-4,5,6-pyrimidinetriamine

Product 1

HCID 178473461HCID 178473461, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of the product of example 5, step (c) (10.5 g) in acetonitrile (50 ml) and triethylamine (17 ml) was added to an ice cold stirred solution of ethoxycarbonylisothiocyanate (3 ml) in acetonitrile (50 ml). This mixture was then stirred at room temperature for 20 min. Diisopropylcarbodiimide (4.5 ml) was then added and the reaction mixture was stirred at reflux for 2 hr and allowed to cool. The reaction mixture was evaporated to dryness and purified by flash chromatography on silica gel (ethyl acetate:dichloromethane, 1:1) to yield the sub-titled compound as a yellow solid (3.0 g).

Workup

  1. stirringthe reaction mixture was stirred
  2. temperatureat reflux for 2 hr
  3. temperatureto cool
  4. customThe reaction mixture was evaporated to dryness
  5. custompurified by flash chromatography on silica gel (ethyl acetate:dichloromethane, 1:1)

Sources & evidence

ORD record
ord-aff72cbdeaa648a788c164f18094cde2
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

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