Benzyl isocyanate → HCID 178522837, compound

HRID 1068928Notes

Reaction equation

HRID 1068928 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[NH:4][N:3]=1.[CH2:19]([N:26]=[C:27]=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCOCC1.CN1C(=O)N(C)CC1>[CH2:19]([NH:26][C:27]([NH:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[NH:4][N:3]=1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 178509242HCID 178509242, compound

Product 1

HCID 178522837HCID 178522837, compound

Reagents, catalysts & solvents 2

HCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 312751,4-DioxaneSolvent

Procedure

With the exclusion of moisture, 261 mg (1.00 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6) are dissolved in 2.5 ml of dioxane and 1 ml of DMEU; 138 μl (1.1 mmol) of benzyl isocyanate are added and the reaction mixture is stirred at RT overnight. The dioxane is evaporated off from the reaction mixture in a rotary evaporator. The resulting yellow solution is poured into 75 ml of water and the product that precipitates is filtered off. Stirring in boiling ethyl acetate yields 3-(benzylamino-carbonylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine; HPLC:tRet(grad20-100)=9.5; FAB-MS: (M+H)+=394.

Workup

  1. customThe dioxane is evaporated off from the reaction mixture in a rotary evaporator
  2. additionThe resulting yellow solution is poured into 75 ml of water
  3. customthe product that precipitates
  4. filtrationis filtered off
  5. stirringStirring

Sources & evidence

ORD record
ord-534566f842d842e68e7c15ca96fc1336
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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