Pyridine → HCID 56959489, compound

HRID 1775751Notes

Reaction equation

HRID 1775751 reaction equation
[OH:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[CH:14]=[C:13]3[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=4)[O:17][C:12]3=[N:11][C:10]2=[O:29])[CH2:3]1.N1C=CC=CC=1.[O:36]([C:38]1[CH:59]=[CH:58][C:41]([C:42](Cl)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)=[CH:40][CH:39]=1)[CH3:37]>ClCCl>[CH3:50][O:49][C:46]1[CH:45]=[CH:44][C:43]([C:42]([C:41]2[CH:40]=[CH:39][C:38]([O:36][CH3:37])=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:8][CH2:7][C@H:6]2[O:5][C@@H:4]([N:9]3[CH:14]=[C:13]4[CH:15]=[C:16]([C:18]5[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:22][CH:23]=5)[O:17][C:12]4=[N:11][C:10]3=[O:29])[CH2:3][C@@H:2]2[OH:1])=[CH:48][CH:47]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 493485CF-1743

Product 1

HCID 56959489HCID 56959489, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 50 L reactor was charged with 2.8 kg (7.03 mol) of 3-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-6-(4-pentylphenyl)furo[2,3-d]pyrimidin-2(3H)-one, 2.8 kg (35.4 mol) of pyridine and 22.4 kg of dichloromethane. The mixture was stirred and to it was added 2.86 kg (8.44 mol) 4,4′-dimethoxyltritylchloride (DMT-Cl) in 14.9 kg dichloromethane at room temperature (rt). After addition, the mixture was stirred for 0.5 h at rt. The mixture was filtered and the filtrate was washed with brine. The filtrate contained the desired product which was used directly in the next step.

Workup

  1. additionAfter addition
  2. stirringthe mixture was stirred for 0.5 h at rt
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed with brine

Sources & evidence

ORD record
ord-ceffa7e27f8e4eb29da309a85c70bd63
Source dataset
uspto-grants-2016_02
Patent number
US09260469B2

Reaction notes

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