Tetrahydrofuran → HCID 69597171, compound

HRID 1793117Notes

Reaction equation

HRID 1793117 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](C=O)=[CH:10][N:9]=1.C([Mg]Br)=C.[Cl-].[NH4+].[O:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>>[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:35]([CH2:34][OH:33])[CH:36]=[CH2:37])=[CH:10][N:9]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 86587299(S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidineHCID 178418507HCID 178418507, compound

Product 1

HCID 69597171HCID 69597171, compound

Conditions

Temperature
0 °C

Procedure

A solution of (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-5-formyl-4-(3-chloro-4-methoxybenzylamino)pyrimidine (4.1 g) in tetrahydrofuran (30 ml) is added to a solution of vinyl magnesium bromide in tetrahydrofuran (43.5 ml) at 0° C., and the mixture is stirred at 0° C. for 1 hour. To the mixture is added a saturated aqueous ammonium chloride solution, and the mixture is extracted with ethyl acetate. The extract is washed with water and then brine, and dried over sodium sulfate. Sodium sulfate is removed by filtration, and the filtrate is concentrated in vacuo. The residue is purified by column chromatography (silica gel, 100 g; ethyl acetate→ethyl acetate:methanol=20:1, and then silica gel, 50 g; chloroform:methanol=50:1) to give (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-5-(1-hydroxymethyl-2-propen-1-yl)-4-(3-chloro-4-methoxybenzylamino)pyrimidine (2.70 g) as colorless amorphous. MS(APCI): 405 (MH+).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. dry with materialbrine, and dried over sodium sulfate
  4. customSodium sulfate is removed by filtration
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe residue is purified by column chromatography (silica gel, 100 g

Sources & evidence

ORD record
ord-0e5e586dc80948d58ac7c0774a324757
Source dataset
uspto-grants-2006_07
Patent number
US07078522B2

Reaction notes

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