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Pivalaldehyde → 4-(3-chloro-phenylamino)-3-(2,2-dimethylpropyl-amino)-1H-pyrazolo[3,4-d]pyrmidine

HRID 1068933
Notes
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Reaction equation

HRID 1068933 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][C:20]([CH:23]=O)([CH3:22])[CH3:21].[BH3-]C#N.[Na+].N1C2C=NC=NC=2C=N1>CN1C(=O)N(C)CC1.CO.CCCCCC.C(O)(=O)C>[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][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]=23)[CH:17]=[CH:16][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 12417Pivalaldehyde2×HCID 5003444Sodium cyanoborohydride2×HCID 210839761H-pyrazolo(4,3-d)pyrimidineHCID 178509242HCID 178509242, compound

Product 1

HCID 696959324-(3-chloro-phenylamino)-3-(2,2-dimethylpropyl-amino)-1H-pyrazolo[3,4-d]pyrmidine

Reagents, catalysts & solvents 3

HCID 176
Acetic Acid
Solvent
2×
HCID 8058HexaneSolvent
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), 129 mg (1.5 mmol) of pivaldehyde 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. Since, according to HPLC, the reaction is incomplete, 129 mg of pivaldehyde, 180 mg of acetic acid and 440 mg of NaCNBH3 are added a number of times until HPLC indicates that all the pyrazolo-pyrimidine has reacted. Between the individual additions, the reaction mixture is stirred at boiling temperature for 20 hours each time. Analogous working-up and stirring in hexane yield 4-(3-chloro-phenylamino)-3-(2,2-dimethylpropyl-amino)-1H-pyrazolo[3,4-d]pyrmidine; m.p. 229-231° C.; HPLC: tRet(grad20-100/20)=11.6; FAB-MS: (M+H)+=331.

Workup

  1. customhas reacted
  2. customfor 20 hours

Sources & evidence

ORD record
ord-1375eb25c0ac451791375db652d11df5
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06251911B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes