Acetic Acid → 4-(3-chloro-phenyl-amino)-3-(n-hexyl-amino)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1068934Notes

Reaction equation

HRID 1068934 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.[CH3:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=O.C(O)(=O)C.[BH3-]C#N.[Na+]>CN1C(=O)N(C)CC1.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]([NH:1][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6184HexanalHCID 5003444Sodium cyanoborohydrideHCID 178509242HCID 178509242, compound

Product 1

HCID 211906194-(3-chloro-phenyl-amino)-3-(n-hexyl-amino)-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 131722711DMEU methanolSolvent

Procedure

Analogously to Example 34, 261 mg (1.00 mmol) of 3-amino-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6), 150 mg (1.5 mmol) of capronaidehyde and 180 mg of acetic acid are stirred in 39 ml of DMEU/methanol (1:2) and then reacted with 440 mg (7 mmol) of NaCNBH3. Stirring in DIPE yields 4-(3-chloro-phenyl-amino)-3-(n-hexyl-amino)-1H-pyrazolo[3,4-d]pyrimidine; HPLC: tRet(grad20-100)=9.9; FAB-MS: (M+H)+=345.

Sources & evidence

ORD record
ord-f92de4dfe93a4c748b768f97dbe2d20b
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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