Acetic Acid → 4-(3-chloro-phenylamino)-3-(cyclohexyl-methyl-amino)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1068932Notes

Reaction equation

HRID 1068932 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.[CH:19]1(C=O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[C:27](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]([N:1]([CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[CH3:27])[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 16275CyclohexanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178509242HCID 178509242, compound

Product 1

HCID 211906924-(3-chloro-phenylamino)-3-(cyclohexyl-methyl-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-chloro-phenylamino)-1 H-pyrazolo[3,4-d]pyrimidine (see Step 1.6), 168 mg (1.5 mmol) of cyclo-hexanecarbaldehyde 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-phenylamino)-3-(cyclohexyl-methyl-amino)-1H-pyrazolo[3,4-d]pyrimidine; m.p. 188-190° C.; HPLC: tRet(grad20-100/20)=12.8; FAB-MS: (M+H)+=357.

Sources & evidence

ORD record
ord-63b4b934732c438a97694674791787d2
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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