Acetic Acid → HCID 19610651, compound

HRID 1602240Notes

Reaction equation

HRID 1602240 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.C(O)(=O)C.[OH:23][C:24]1[C:31]([O:32][CH3:33])=[CH:30][C:27]([CH:28]=O)=[CH:26][C:25]=1[O:34][CH3:35].[BH3-]C#N.[Na+]>CO.CN1C(=O)N(C)CC1>[Cl:18][C:14]1[CH:13]=[C:12]([NH:11][C:9]2[N:8]=[CH:7][N:6]=[C:5]3[NH:4][N:3]=[C:2]([NH:1][CH2:28][C:27]4[CH:26]=[C:25]([O:34][CH3:35])[C:24]([OH:23])=[C:31]([O:32][CH3:33])[CH:30]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8655SyringaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178509242HCID 178509242, compound

Product 1

HCID 19610651HCID 19610651, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

Analogously to Example 21, 1.00 mmol of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine in 26 ml of methanol, 13 ml of DMEU and 3.0 mmol of acetic acid are first reacted with 4-hydroxy-3,5-dimethoxy-benzaldehyde and then reduced with 7.00 mmol of NaCNBH3 (5-7 days). 4-(3-Chloro-phenylamino)-3-(4-hydroxy-3,5-dimethoxy-benzylamino)-1H-pyrazolo[3,4-d]pyrimidine is obtained; HPLC: TRet (Grad5-40)=17.0.

Sources & evidence

ORD record
ord-96d5ba40f9da4344ac4c108834946f19
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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