Sodium hydride → HCID 22349793, compound

HRID 896075Notes

Reaction equation

HRID 896075 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[H-].[Na+].[C:13]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].C(N(CC)C(C)C)(C)C>O1CCCC1>[NH2:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([NH:1][C:21]([C:20]2[CH:24]=[CH:25][C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:18][CH:19]=2)=[O:22])[CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 704972-Methylthiopyrimidine-4,6-diamineHCID 743724-tert-Butylbenzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 22349793HCID 22349793, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4,6-diamino-2-methylmercaptopyrimidine (50 mg, 0.032 mmol) in anhydrous tetrahydrofuran was added sodium hydride, followed by the addition of 4-t-butylbenzoyl chloride (0.084 mL, 0.32 mmol) and N, N-diisopropylethylamine. The mixture was heated at 50° C. for 16 hours after which it was subjected to aqueous work up. The product was extracted with ethyl acetate and purified by HPLC to give N-(6-amino-2-methylthiopyrimidin-4-yl)[4-(tert-butyl)phenyl]carboxamide. M+1=317.3.

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-cbd6dbb1241b4d89834b5ee97f9a3760
Source dataset
uspto-grants-2005_07
Patent number
US06919339B2

Reaction notes

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