4,6-Dichloro-5-pyrimidinecarbaldehyde → 4-(4-Chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid isopropyl ester

HRID 1931590Notes

Reaction equation

HRID 1931590 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([NH:13][NH2:14])[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].Cl.C(OC(N1CCC(NN)CC1)=O)(C)C.[Cl:30][C:31]1[C:36]([CH:37]=O)=[C:35](Cl)[N:34]=[CH:33][N:32]=1.ClC1N=CN=C2N(C3CCC(C4ON=C(C(C)C)N=4)CC3)N=CC=12>>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([N:13]2[C:35]3=[N:34][CH:33]=[N:32][C:31]([Cl:30])=[C:36]3[CH:37]=[N:14]2)[CH2:11][CH2:12]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde2×HCID 57964906HCID 57964906, compoundHCID 57965012HCID 57965012, compound2×HCID 669152794-Hydrazino-piperidine-1-carboxylic acid isopropyl ester hydrochloride

Product 1

HCID 575444174-(4-Chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid isopropyl ester

Procedure

4-(4-Chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid isopropyl ester was prepared from the reaction of 4-hydrazino-piperidine-1-carboxylic acid isopropyl ester (Intermediate 10) and 4,6-dichloro-pyrimidine-5-carbaldehyde (Intermediate 16) using the procedure described for 4-chloro-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 23). The product was purified by flash chromatography eluting with 40% ethyl acetate/hexanes to give 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid isopropyl ester as a white solid. Mass spectrum M+=323.0.

Workup

  1. customThe product was purified by flash chromatography
  2. washeluting with 40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fdf69e61d9304c429f1f7bb45cecc4f3
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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