Sodium Carbonate → HCID 44225400, compound

HRID 880521Notes

Reaction equation

HRID 880521 reaction equation
I[C:2]1[C:10]2[C:9]([NH2:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.[CH3:15][NH:16][C:17]([NH:19][C:20]1[S:21][C:22]2[CH:28]=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:26]=[CH:25][C:23]=2[N:24]=1)=[O:18].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[NH2:11][C:9]1[C:10]2[C:2]([C:27]3[CH:26]=[CH:25][C:23]4[N:24]=[C:20]([NH:19][C:17]([NH:16][CH3:15])=[O:18])[S:21][C:22]=4[CH:28]=3)=[CH:3][N:4]([CH:12]([CH3:14])[CH3:13])[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 58279572HCID 58279572, compoundHCID 58279576HCID 58279576, compound

Product 1

HCID 44225400HCID 44225400, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (302) (200 mg, 0.66 mmol), 1-methyl-3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)urea (J-2) (333 mg, 1.5 eq, 1.0 mmol), Pd(PPh3)4 (76 mg, 0.1 eq, 0.066 mmol) and Na2CO3 (2 N, 2 mL) in DME (10 mL) was stirred at reflux for 30 min under Ar. The mixture was cooled to room temperature, and then concentrated in vacuo. Brine (10 mL) was added to the residue and then extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with brine (10 mL), dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography eluting with MeOH/DCM (1/30) to afford the desired product, 1-(6-(4-amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzo[d]thiazol-2-yl)-3-methylurea (303) (147 mg 58% yield) as a white solid ESI-MS m/z: 382.00 [M+H]+.

Workup

  1. temperatureat reflux for 30 min under Ar
  2. concentrationconcentrated in vacuo
  3. additionBrine (10 mL) was added to the residue
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. washThe combined organic layer was washed with brine (10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe residue was purified by flash column chromatography
  10. washeluting with MeOH/DCM (1/30)

Sources & evidence

ORD record
ord-0491d18480e34b56a5ffda641ae70eeb
Source dataset
uspto-grants-2015_03
Patent number
US08993580B2

Reaction notes

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