1-Propanol → HCID 9800958, compound

HRID 2300847Notes

Reaction equation

HRID 2300847 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23](I)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:26]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27]1.C([O-])([O-])=O.[K+].[K+].C(O)CC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O.O>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:28]5[CH:29]=[CH:30][S:26][CH:27]=5)=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 10311-PropanolHCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 59924653HCID 59924653, compound

Product 1

HCID 9800958HCID 9800958, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 2-[(S)-1-phenylethylamino]-4-[5-iodobenzimidazol-1-yl]pyrimidine (EXAMPLE 271) (37 mg), 3-thiophene boronic acid (16 mg), K2CO3 (35 mg) and Pd(PPh3)4 (0.97 mg) in 1:1 n-propanol:water (4 mL) was stirred under N2 at 100° C. for 16 h. The reaction mixture was cooled and poured into 100 mL EtOAc and washed with water, then brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The product was purified by silica gel chromatography eluting successively with 10% acetone/hexanes, 20% acetone/hexanes and 30% acetone/hexanes giving 25.3 mg of the title compound. Mass spectrum (ESI): 398.1 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by silica gel chromatography
  7. washeluting successively with 10% acetone/hexanes, 20% acetone/hexanes and 30% acetone/hexanes giving 25.3 mg of the title compound

Sources & evidence

ORD record
ord-c485cb4ba3534f01afc4c4b4c63d6131
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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