Water → HCID 18186495, compound

HRID 1357543Notes

Reaction equation

HRID 1357543 reaction equation
C([SiH](CC)CC)C.[NH:8]([C:15]1[C:20]([CH:21](O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:19][N:18]=[C:17]([Cl:29])[N:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O>[NH:8]([C:15]1[C:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:19][N:18]=[C:17]([Cl:29])[N:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 18186475HCID 18186475, compound

Product 1

HCID 18186495HCID 18186495, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (0.14 ml, 1.10 mmol) was added to a solution of 4-anilino-2-chloro-5-[1-hydroxy-1-phenylmethyl]pyrimidine (Method 58; 170 mg, 0.55 mmol) in trifluoroacetic acid (1.5 ml), and the mixture was stirred for 64 hours. Water (20 ml) was added and the mixture was neutralised with sodium carbonate powder and extracted with DCM (3×20 ml). The extracts were combined, washed with water (30 ml), dried, concentrated to a volume of 5 ml, and loaded on a Varian Mega Bond Elut column. Elution with DCM and concentration of the appropriate fractions gave the product as a yellow crystalline solid (42 mg, 26%). NMR (CDCl3): 3.93 (s, 2H), 6.45 (br s, 1H), 7.08 (m, 1H), 7.2-7.4 (m, 9H), 8.09 (s, 1H); MS (MH+): 296.2, 298.2.

Workup

  1. extractionextracted with DCM (3×20 ml)
  2. washwashed with water (30 ml)
  3. customdried
  4. concentrationconcentrated to a volume of 5 ml
  5. washElution with DCM and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-c61e4510b3ce437ea70b00085f0dfc7c
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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