1,2-Dichlorobenzene → HCID 178448370, compound

HRID 1068881Notes

Reaction equation

HRID 1068881 reaction equation
C(OC([NH:11][C@H:12]([C:16]([NH:18][C:19]1[C:27]2[C:22](=[N:23][CH:24]=[N:25][C:26]=2[NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)[NH:21][N:20]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1.ClC1C=CC=CC=1Cl>C1COCC1.CN1C(=O)N(C)CC1.[Pd]>[Cl:35][C:31]1[CH:30]=[C:29]([NH:28][C:26]2[N:25]=[CH:24][N:23]=[C:22]3[NH:21][N:20]=[C:19]([NH:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH2:11])[C:27]=23)[CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 178448373HCID 178448373, compound

Product 1

HCID 178448370HCID 178448370, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 67065082Thf dmeuSolvent

Procedure

In 4 ml of THF/DMEU 1:3, 40 mg (0.08 mmol) of rac.-3-([N-benzyloxycarbonylvalyl]-amino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Example 8) are hydrogenated in the presence of 10 mg of Pd/C (10%) and 10 μl of 1,2-dichlorobenzene. The catalyst is filtered off, and the filtrate is partially concentrated by evaporation in a rotary evaporator, poured into 30 ml of water and again filtered and the filtrate is concentrated by evaporation under a high vacuum first at RT and finally at 50° C. to yield rac.-4-(3-chlorophenylamino)-3-(valyl-amino)-1H-pyrazolo[3,4-d]pyrimidine; HPLC: tRet(grad20-100/20)=9.2; FAB-MS: (M+H)+=360.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is partially concentrated by evaporation in a rotary evaporator
  3. additionpoured into 30 ml of water
  4. filtrationagain filtered
  5. concentrationthe filtrate is concentrated by evaporation under a high vacuum first at RT and finally at 50° C.

Sources & evidence

ORD record
ord-c946c04900d1407caa10da05bb6e9887
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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