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

HRID 497730Notes

Reaction equation

HRID 497730 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 example 2, 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 .5 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. additionadded
  5. customprecipitated which
  6. customwas isolated by filtration
  7. dry with materialdried over P2O5 at 50° C.

Sources & evidence

ORD record
ord-04ccf1a95cba4a148500d4046160114a
Source dataset
uspto-grants-2005_09
Patent number
US06949643B2

Reaction notes

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