Acetic Acid → HCID 19610641, compound

HRID 1602241Notes

Reaction equation

HRID 1602241 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.[CH2:23]1[O:33][C:32]2[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][C:25]=2[O:24]1.[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:30]=[CH:31][C:32]5[O:33][CH2:23][O:24][C:25]=5[CH:26]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8438PiperonalHCID 5003444Sodium cyanoborohydrideHCID 178509242HCID 178509242, compound

Product 1

HCID 19610641HCID 19610641, 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 3,4-methylenedioxy-benzaldehyde and then reduced with 7.00 mmol of NaCNBH3 (5-7 days). 4-(3-Chloro-phenylamino)-3-(3,4-methylenedioxybenzylamino)-1H-pyrazolo[3,4-d]pyrimidine is obtained; m.p. 220-222° C.; HPLC: TRet (Grad5-40)=22.5° C.

Sources & evidence

ORD record
ord-d5da336d7791476fb3c4d5d098f79fa4
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

Loading…