Acetic Acid → 4-(3-Chloro-phenylamino)-3-[4-(2-methyl-tetrazol-5-yl)-benzylamino]-1H-pyrazolo[3,4-d]pyrimidine

HRID 1068901Notes

Reaction equation

HRID 1068901 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][N:20]1[N:24]=[N:23][C:22]([C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)=[N:21]1.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][CH2:29][C:28]4[CH:27]=[CH:26][C:25]([C:22]5[N:23]=[N:24][N:20]([CH3:19])[N:21]=5)=[CH:32][CH:31]=4)[C:10]=23)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 104878484-(2-Methyl-2H-tetrazol-5-yl)-benzaldehydeHCID 178509242HCID 178509242, compound

Product 1

HCID 211905864-(3-Chloro-phenylamino)-3-[4-(2-methyl-tetrazol-5-yl)-benzylamino]-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 131722711DMEU methanolSolvent

Procedure

Analogously to Example 34, 261 mg (1.00 mmol) of 3amino-4-(3-chlorophenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 1.6), 282 mg (1.5 mmol) of 4-(2-methyl-2H-tetrazol-5-yl)-benzaldehyde and 180 mg of acetic acid are stirred in 39 ml of DMEU/methanol (1:2) at RT for 1 hour and then reacted with two 440 mg (7 mmol) portions of NaCNBH3. 4-(3-Chloro-phenylamino)-3-[4-(2-methyl-tetrazol-5-yl)-benzylamino]-1H-pyrazolo[3,4-d]pyrimidine is obtained; m.p. 232-235° C.; HPLC: tRet(grad20-100/20)=11.4; FAB-MS: (M+H)+=433.

Sources & evidence

ORD record
ord-6480c275849340019f8a92ccec322d08
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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