Sodium Bicarbonate → (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-(1-hydroxypentyl)pyrimidine

HRID 431060Notes

Reaction equation

HRID 431060 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)[C:11]([CH:25]=[O:26])=[CH:10][N:9]=1.[CH2:27]([Li])[CH2:28][CH2:29][CH3:30].C(=O)([O-])O.[Na+]>OC[C@@H]1CCCN1C1N=C(NCC2C=CC(OC)=C(Cl)C=2)C(C(=O)C)=CN=1.CCCCCC>[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)[C:11]([C@@H:25]([OH:26])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 86587299(S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidineHCID 178418339Butyllithium

Product 1

HCID 69370668(S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-(1-hydroxypentyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 69370083(S)-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidineSolvent

Procedure

A solution of (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidine (10.0 mg) in tetrahydrofuran (1.0 ml) obtained in Example 2 (3) is treated with a 1.6M solution of n-butyl lithium in hexane (83 μl) at −78° C. for 3 minutes, and thereto is added an aqueous sodium hydrogen carbonate solution. The reaction mixture is extracted with ethyl acetate to give (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-(1-hydroxypentyl)pyrimidine (13.7 mg) as oil.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate

Sources & evidence

ORD record
ord-c7f607288f154458acef142e091087ad
Source dataset
uspto-grants-2003_12
Patent number
US06656935B2

Reaction notes

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