Hydrochloric Acid → 4-amino-2-[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone

HRID 1814237Notes

Reaction equation

HRID 1814237 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[C:13]([NH2:19])[N:12]=1.[C:20](OCC)(=O)[CH:21]=[O:22].O.Cl>[Na].CO>[NH2:17][C:15]1[C:14]2[N:18]=[CH:20][C:21](=[O:22])[NH:19][C:13]=2[N:12]=[C:11]([S:10][CH2:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[N:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 70211Ethyl oxoacetateHCID 222885032-[[(2,3-Difluorophenyl)methyl]thio]-4,5,6-pyrimidinetriamine

Product 1

HCID 223200814-amino-2-[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5360545SodiumSolvent

Procedure

The product of step (c) (100 mg) was dissolved in a solution of sodium (0.05 g) in methanol (5 ml). This was left to stir for 15 min at room temperature, then ethyl glyoxalate (134 μl) was added to the mixture which was left to stir for 12 hr at room temperature. Water (5 ml) was added, then concentrated hydrochloric acid was slowly added to acidify the solution to ˜pH5 whereupon a solid precipitated which was isolated by filtration and dried over P2O5 at 50° C. to yield a pale yellow solid (44.5 mg).

Workup

  1. waitThis was left
  2. waitwas left
  3. stirringto stir for 12 hr at room temperature
  4. customprecipitated which
  5. customwas isolated by filtration
  6. dry with materialdried over P2O5 at 50° C.

Sources & evidence

ORD record
ord-34953e5be5104b1cb4c48a97817ebf23
Source dataset
uspto-grants-2005_04
Patent number
US06875868B2

Reaction notes

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