Iodoethane → Isopropyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl(ethyl)carbamate

HRID 346541Notes

Reaction equation

HRID 346541 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:14])[O:10][CH:11]([CH3:13])[CH3:12])=[C:6]([NH2:15])[N:5]=[C:4]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:17]=2)[N:3]=1.[H-].[Na+].I[CH2:36][CH3:37]>>[NH2:1][C:2]1[C:7]([N:8]([CH2:36][CH3:37])[C:9](=[O:14])[O:10][CH:11]([CH3:13])[CH3:12])=[C:6]([NH2:15])[N:5]=[C:4]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:17]=2)[N:3]=1

Participants

4

Reactant 3

HCID 6340Iodoethane2×HCID 24758Sodium hydride2×HCID 17973417Isopropyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinylcarbamate

Product 1

HCID 21081987Isopropyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl(ethyl)carbamate

Procedure

Prepared in analogy to Example 6 with 60 mg (0.14 mmol) of isopropyl 4,6-diamino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinylcarbamate from Example 3, 4.95 mg (0.21 mmol) of sodium hydride and 21.4 mg (0.17 mmol) of iodoethane. To complete the reaction, the same amount of sodium hydride and iodoethane are added once again. The residue is purified by preparative RP-HPLC.

Workup

  1. customthe reaction
  2. customThe residue is purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-4c8d4cbab3c140fa8c30a9066e166cce
Source dataset
uspto-grants-2007_02
Patent number
US07173037B2

Reaction notes

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