3-Bromopyridine → HCID 21913309, compound

HRID 1008091Notes

Reaction equation

HRID 1008091 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:22][C:23]#[CH:24])[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]3[N:15]=[N:16][N:17]=[C:9]3[C:8]=2[N:18]=1)[CH3:2].C(OCCNC(=O)OC(C)(C)C)C#C.Br[C:40]1[CH:41]=[N:42][CH:43]=[N:44][CH:45]=1.BrC1C=NC=CC=1>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:22][C:23]#[C:24][C:40]2[CH:41]=[N:42][CH:43]=[N:44][CH:45]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]3[N:15]=[N:16][N:17]=[C:9]3[C:8]=2[N:18]=1)[CH3:2]

Participants

5

Reactant 4

HCID 122863-BromopyridineHCID 783445-BromopyrimidineHCID 21913133HCID 21913133, compoundHCID 21913902Carbamic acid, [2-(2-propynyloxy)ethyl]-, 1,1-dimethylethyl ester (9CI)

Product 1

HCID 21913309HCID 21913309, compound

Procedure

The method described in Part B of Example 81 was followed. 8-Ethoxymethyl-5,6-dimethyl-7-(2-prop-2-ynyloxyethyl)-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridine (5.5 g, 17 mmol) was used as the starting material in lieu of tert-butyl 2-(prop-2-ynyloxy)ethylcarbamate, and 5-bromopyrimidine was used in lieu of 3-bromopyridine. The crude product was purified by column chromatography on silica gel (620 g, eluting with 98:2 dichloromethane:methanol), and the resulting solid was mixed with 2-propanol (150 mL). Insoluble impurities were removed by filtration, and the solution was concentrated to a volume of 20 mL. The product crystallized and was isolated by filtration and washed with 2-propanol and diethyl ether to provide 6.10 g of 8-ethoxymethyl-5,6-dimethyl-7-[2-(3-pyrimidin-5-ylprop-2-ynyloxy)ethyl]-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridine as white crystals.

Workup

  1. customThe crude product was purified by column chromatography on silica gel (620 g, eluting with 98:2 dichloromethane:methanol)
  2. additionthe resulting solid was mixed with 2-propanol (150 mL)
  3. customInsoluble impurities were removed by filtration
  4. concentrationthe solution was concentrated to a volume of 20 mL
  5. customThe product crystallized
  6. customwas isolated by filtration
  7. washwashed with 2-propanol and diethyl ether

Sources & evidence

ORD record
ord-80f4f573fce14113aadc76b8fab86421
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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