[(2r)-2-[[2-[[(3-Chloro-2-fluorophenyl)methyl]thio]-7,8-dihydro-7-oxo-4-pteridinyl]amino]propyl]-carbamic acid, 1,1-dimethylethyl ester → 4-[[(1r)-2-Amino-1-methylethyl]amino]-2-[[(3-chloro-2-fluorophenyl)methyl]thio]-7(8h)-pteridinone, monohydrochloride

HRID 1814251Notes

Reaction equation

HRID 1814251 reaction equation
[Cl:1][C:2]1[C:3]([F:33])=[C:4]([CH2:8][S:9][C:10]2[N:19]=[C:18]([NH:20][C@H:21]([CH3:31])[CH2:22][NH:23]C(=O)OC(C)(C)C)[C:17]3[N:16]=[CH:15][C:14](=[O:32])[NH:13][C:12]=3[N:11]=2)[CH:5]=[CH:6][CH:7]=1>O1CCOCC1.Cl.O>[ClH:1].[NH2:23][CH2:22][C@H:21]([NH:20][C:18]1[C:17]2[N:16]=[CH:15][C:14](=[O:32])[NH:13][C:12]=2[N:11]=[C:10]([S:9][CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:33])[N:19]=1)[CH3:31]

Participants

5

Reactant 1

HCID 91168650[(2r)-2-[[2-[[(3-Chloro-2-fluorophenyl)methyl]thio]-7,8-dihydro-7-oxo-4-pteridinyl]amino]propyl]-carbamic acid, 1,1-dimethylethyl ester

Product 1

HCID 1317248214-[[(1r)-2-Amino-1-methylethyl]amino]-2-[[(3-chloro-2-fluorophenyl)methyl]thio]-7(8h)-pteridinone, monohydrochlorideYield 175.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A two-phase mixture of the product from Example 9 (76 mg) in 1,4-dioxane (3 ml) and conc. HCl (0.3 ml) was stirred for 2 hours, then diluted with water (10 ml) and lyophilised. The residue was dissolved in water (10 ml), washed with ethyl acetate (5 ml), and lyophilised to give the titled compound as a pale yellow solid (58 mg).

Workup

  1. washwashed with ethyl acetate (5 ml)

Sources & evidence

ORD record
ord-bb6c530a29d84e7385762ea8cae1f4b7
Source dataset
uspto-grants-2005_04
Patent number
US06875868B2

Reaction notes

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