Water → HCID 57986816, compound

HRID 871946Notes

Reaction equation

HRID 871946 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH:4]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH:24]=[N:23][N:22]=[N:21]4)=[CH:16][CH:15]=3)[N:11]=2)[CH2:3]1.ClC1N=[CH:30][CH:29]=[CH:28][N:27]=1.[C:32]([O-])([O-])=O.[K+].[K+].O.C[N:40]([CH:42]=O)[CH3:41]>>[CH2:30]([C:29]1[CH:41]=[N:40][C:42]([N:2]2[CH2:6][CH2:5][CH:4]([C:7]3[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]4[CH:15]=[CH:16][C:17]([N:20]5[CH:24]=[N:23][N:22]=[N:21]5)=[CH:18][CH:19]=4)[N:11]=3)[CH2:3]2)=[N:27][CH:28]=1)[CH3:32]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 66911098HCID 66911098, compound

Product 1

HCID 57986816HCID 57986816, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 1-[4-(2-Pyrrolidin-3-yl-thiazol-4-ylmethoxy)-phenyl]-1H-tetrazole hydrochloride (From Step 1) (350 mg, 0.959 mmol), 2-chloropyrimidine (0.23 mL, 2.0 eq.) and K2CO3 (398 mg, 2.88 mmol) in DMF (5 mL) was heated at 90° C. for 4 hours. Water was added and the solution was extracted with ethyl acetate, separated, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (50:50 EtOAc/hexanes) to afford the desired product. 1H NMR (CDCl3): δ 8.91 (1H, s), 8.21 (2H, s), 7.62 (2H, d), 7.27 (1H, s), 7.17 (2H, d), 5.24 (2H, s), 4.12 (1H, m), 3.98 (1H, m), 3.87 (2H, m), 3.69 (1H, m), 2.56 (1H, m), 2.47 (2H, m), 2.37 (1H, m), 1.21 (3H, t).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. customseparated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (50:50 EtOAc/hexanes)

Sources & evidence

ORD record
ord-a07d5cff680940c9beb7d5dcc379d818
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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