(R)-(-)-2-Amino-1-propanol → 2-[[(2,3-Difluorophenyl)methyl]thio]4-[[(1R)-2-hydroxy-1-methylethyl]amino]-7(8H)-pteridinone

HRID 1814240Notes

Reaction equation

HRID 1814240 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:20]=[C:19](SCC2C=CC=C(F)C=2F)[C:18]2[N:17]=[CH:16][C:15](=[O:31])[NH:14][C:13]=2[N:12]=1.[NH2:32][C@@H:33]([CH2:35][OH:36])[CH3:34]>>[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:20]=[C:19]([NH:32][C@H:33]([CH3:34])[CH2:35][OH:36])[C:18]2[N:17]=[CH:16][C:15](=[O:31])[NH:14][C:13]=2[N:12]=1

Participants

3

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 225060122,4-Bis[[(2,3-difluorophenyl)methyl]thio]-7(8h)-pteridinone

Product 1

HCID 444550142-[[(2,3-Difluorophenyl)methyl]thio]4-[[(1R)-2-hydroxy-1-methylethyl]amino]-7(8H)-pteridinoneYield 11.7%

Procedure

The product of example 2, step (g) (2.3 g) and D-alaninol (5 g) were microwaved at 150° C. for 5 min. The resulting solution was partitioned between ethyl acetate and aqueous ammonium chloride and the organic layer was washed with ammonium chloride (2×50 ml). The organic layer was evaporated to dryness and purified twice by silica gel chromatography using first 20:1 DCM:methanol and then 1:1 DCM:ethyl acetate to yield the titled compound (220 mg).

Workup

  1. customThe resulting solution was partitioned between ethyl acetate and aqueous ammonium chloride
  2. washthe organic layer was washed with ammonium chloride (2×50 ml)
  3. customThe organic layer was evaporated to dryness
  4. custompurified twice by silica gel chromatography

Sources & evidence

ORD record
ord-6d9d47de6ef84e8da81b6902b1f511f6
Source dataset
uspto-grants-2005_04
Patent number
US06875868B2

Reaction notes

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