Water → HCID 57986816, compound

HRID 1408374Notes

Reaction equation

HRID 1408374 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-c9c1af15c53e46589f1b8a8717fac338
Source dataset
uspto-grants-2014_12
Patent number
US08921350B2

Reaction notes

Loading…