Sodium Bicarbonate → HCID 11336703, compound

HRID 254174Notes

Reaction equation

HRID 254174 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][Si](C(C)(C)C)(C)C)[N:13]=2)=[O:9])[CH:5]=[C:4]([C:27]2[O:28][C:29]([CH3:32])=[CH:30][CH:31]=2)[N:3]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C.C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][OH:19])[N:13]=2)=[O:9])[CH:5]=[C:4]([C:27]2[O:28][C:29]([CH3:32])=[CH:30][CH:31]=2)[N:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 11248001HCID 11248001, compound

Product 1

HCID 11336703HCID 11336703, compoundYield 116.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-6-(5-methyl-2-furyl)-N-(6-(tert-butyldimethylsilyloxymethyl)pyridin-2-ylmethyl)pyrimidine-4-carboxamide (614 mg, 1.36 mmol) in acetic acid (9 mL) water (3 mL) and THF (3 mL) was stirred at room temperature for 4 days, neutralised with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic phase was dried (MgSO4), concentrated in vacuo, and the resulting solid triturated with MeOH and filtered to give the title compound (536 mg, 49%) as a cream solid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe resulting solid triturated with MeOH
  5. filtrationfiltered

Sources & evidence

ORD record
ord-487fbd18de294342ad45c33959d2187a
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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