Ethanol → 1H-Pyrazolo(3,4-d)pyrimidine

HRID 1068880

Reaction equation

HRID 1068880 reaction equation
CN1CCOCC1.ClC(OCC(C)C)=O.N[C:17]1[C:25]2[C:20](=[N:21][CH:22]=[N:23][C:24]=2NC2C=CC=C(Cl)C=2)[NH:19][N:18]=1.C(O)C>C1COCC1.CS(C)=O>[NH:19]1[C:20]2=[N:21][CH:22]=[N:23][CH:24]=[C:25]2[CH:17]=[N:18]1

Participants

7

Reactant 4

HCID 702EthanolHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 178509242HCID 178509242, compound

Product 1

HCID 674991H-Pyrazolo(3,4-d)pyrimidine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Analogously to Example 5, 436 mg (2.3 mmol) of N-ethoxycarbonyl-(D/L)-valine [prepared from (D/L)-valine as described in J. Org. Chem. 60, 7256 (1995)] in 4.8 ml of THF and 506 μl (4.6 mmol) of NMM are activated with 349 μl (2.6 mmol) of isobutyl chloroformate and then reacted with 600 mg (2.3 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6). Dissolution in DMSO (2 ml) at 100° C., addition of 25 ml of ethanol and cooling yield rac.-4-(3-chloro-phenylamino)-3{N-ethoxycarbonyl-valyl)-amino}-1H-pyrazolo[3,4-d]pyrimidine; HPLC: tRet(grad20-100/20)=13.2; FAB-MS: (M+H)+=432.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-e92f522b30754ac385c7aa9aaacb819f
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Linked notes

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