3-Methyluracil → 2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one

HRID 1182661Notes

Reaction equation

HRID 1182661 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][NH:4][C:3]1=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[OH:38][C@@H:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[NH2:44].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[OH:38][C@@H:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[NH:44][C:3]1[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 790663-MethyluracilHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 12886906(1R,2R)-2-aminocyclopentan-1-ol hydrochloride

Product 1

HCID 673709162-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-oneYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyluracil (12.6 mg, 0.1 mmol) was dissolved in 0.5 mL of DMF, and then BOP (71 mg, 0.16 mmol) was added. The mixture was stirred at room temperature for two minutes, then (1R,2R)-(−)-2-hydroxycyclopentylamine hydrochloride salt (22 mg, 0.16 mmol) was added, followed by DBU (51 uL, 3.4 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was purified by a semi-preparative HPLC to give pure product (16 mg, yield 76%). MS (ESI) m/z 210.1 [M+H]+.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe reaction mixture was purified by a semi-preparative HPLC

Sources & evidence

ORD record
ord-b91a2c85966e4a2ba3dd38e25348a084
Source dataset
uspto-grants-2014_03
Patent number
US08664207B2

Reaction notes

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