Sodium Carbonate → HCID 25110819, compound

HRID 1035473Notes

Reaction equation

HRID 1035473 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:17](C(OC(C)(C)C)=O)[CH:16]=1)(=O)[C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH3:13].C(=O)(O)O.[NH2:35][C:36]([NH2:38])=[NH:37]>COCCO>[CH2:10]([C:9]1[CH:8]=[C:7]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[N:37]=[C:36]([NH2:38])[N:35]=1)[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 286947Carbonic acid-guanidine (1:1)HCID 44541418HCID 44541418, compound

Product 1

HCID 25110819HCID 25110819, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

1.2 278 mg (2.0 mmol) of sodium carbonate are added to a solution of 314 mg (0.96 mmol) of tert-butyl 3-hept-2-inoylpyrrolo[2,3-b]pyridine-1-carboxylate and 130 mg (0.72 mmol) of guanidine carbonate in 2 ml of ethylene glycol monomethyl ether, and the mixture is heated at the boil for 24 hours. After cooling, the mixture is partitioned between water and ethyl acetate. The organic phase is dried over sodium sulfate, evaporated, and the residue is chromatographed using preparative HPLC, giving 4-butyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-ylamine (“A1”) as colourless solid; ESI 269;

Workup

  1. temperaturethe mixture is heated at the boil for 24 hours
  2. temperatureAfter cooling
  3. customthe mixture is partitioned between water and ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customthe residue is chromatographed

Sources & evidence

ORD record
ord-7947287e10334623b6810d547de78564
Source dataset
uspto-grants-2013_10
Patent number
US08546390B2

Reaction notes

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