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

HRID 1814241Notes

Reaction equation

HRID 1814241 reaction equation
C([Li])CCC.[F:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:14][S:15][C:16]1[N:21]=[C:20]([NH2:22])[C:19]([N:23]=O)=[C:18]([NH2:25])[N:17]=1.[O:26]1CC[CH2:28][CH2:27]1>CN(C)C=O>[NH2:25][C:18]1[C:19]2[N:23]=[CH:28][C:27](=[O:26])[NH:22][C:20]=2[N:21]=[C:16]([S:15][CH2:14][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([F:13])[C:7]=2[F:6])[N:17]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 222884992-[[(2,3-Difluorophenyl)methyl]thio]-5-nitroso4,6-pyrimidinediamineHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of triethyl phosphonoacetate (15.0 g) in tetrahydrofuran (60 ml) cooled in an ice bath was added butyllithium (2.5 M in hexanes, 25.6 ml) at a rate such that the internal temperature was maintained below 30° C. To this mixture was then added a solution of the product of Example 2 step (b) (10.0 g) in N,N-dimethylformamide (60 ml). The reaction mixture was heated at reflux for 1 hour, then cooled to room temperature and quenched with acetic acid (6 ml). The solid thus precipitated was isolated by filtration, washed with water, ethanol and diethyl ether, and dried over P2O5 at 50° C. to give the sub-titled product as a pale green solid (9.3 g).

Workup

  1. temperaturewas maintained below 30° C
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1 hour
  4. customquenched with acetic acid (6 ml)
  5. customThe solid thus precipitated
  6. customwas isolated by filtration
  7. washwashed with water, ethanol and diethyl ether
  8. dry with materialdried over P2O5 at 50° C.

Sources & evidence

ORD record
ord-eefb6ab9b73943ac926add79ee0d6c90
Source dataset
uspto-grants-2005_04
Patent number
US06875868B2

Reaction notes

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