Acetic Acid → HCID 178478152, compound

HRID 1068911Notes

Reaction equation

HRID 1068911 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.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH:28]=O>CO>[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]([N:1]=[CH:28][C:24]4[S:23][CH:27]=[CH:26][CH:25]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 73642-ThiophenecarboxaldehydeHCID 178509242HCID 178509242, compound

Product 1

HCID 178478152HCID 178478152, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogously to Example 32,261 mg (1.00 mmol) of 3-amino-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6) and 180 mg of acetic acid are dissolved in 26 ml of methanol and reacted with 168 mg (1.5 mmol) of thiophene-2-carbaldehyde to form 4-(3-chloro-phenylamino)-3-[(thien-2-yl)-methyleneamino]-1H-pyrazolo[3,4-d]pyrimidine. Reduction of the above intermediate in 0.15 ml of DMEU with 8 ml (8 mmol) of DIBAL-H, analogous working-up and crystallization from ethyl acetate yield 4-(3-chloro-phenylamino)-3-[(thien-2-yl)-methylamino]-1H-pyrazolo[3,4-d]pyrimidine; m.p. 228-229° C., HPLC: tRet(grad20-100)=8-9; MS: (M)+=356.

Sources & evidence

ORD record
ord-e95473001292425a87503308777a3656
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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