Sodium Carbonate → 5-Bromo-2-[4-(phenylmethoxy)phenyl]pyrimidine

HRID 1603299Notes

Reaction equation

HRID 1603299 reaction equation
BrC1C=NC(I)=NC=1.C(OC1C=CC(B(O)O)=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].F[C:33]1[C:38](F)=[C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]C)[CH:36]=[CH:35][C:34]=1[C:49]1[N:54]=[CH:53][C:52]([Br:55])=[CH:51][N:50]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH2:41]([O:40][C:37]1[CH:38]=[CH:33][C:34]([C:49]2[N:50]=[CH:51][C:52]([Br:55])=[CH:53][N:54]=2)=[CH:35][CH:36]=1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27343144-Benzyloxy-phenylboronic acidHCID 70066515-Bromo-2-iodopyrimidineHCID 232970432-(2',3'-Difluoro-4'-octyloxyphenyl)-5-bromopyrimidine

Product 1

HCID 5640285-Bromo-2-[4-(phenylmethoxy)phenyl]pyrimidineYield 79%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

--Quantities: 5-bromo-2-iodopyrimidine 2 (4.33 g, 15.2 mmol), 4-benzyloxyphenylboronic acid 25 (3.81 g, 16.7 mmol), tetrakis(triphenylphosphine)palladium (351 mg, 0.30 mmol), 2M sodium carbonate (50 ml), DME (50 ml). The experimental procedure was as described for compound 4 to yield the benzyloxyphenylpyrimidine 26 (4.12 g, 79%) (from EtOH), m.p. 155° C.; νmax /cm-1 (KBr) 3200, 1600, 1550, 1520, 1410, 1325, 1250, 1165, 1040, 1025, 1010 and 840; δ 5.14 (2H, s, OCH2), 7.06 (2H, d, J 9, 3'- and 5'-H), 7.30-7.48 (5H, m, PhH), 8.35 (2H, d, J 9, 2'-and 6'-H) and 8.77 (2H, s, 4- and 6-H); m/z 342 (M+), 340 (M+), 249, 221, 196, 142, 115 and 91.

Sources & evidence

ORD record
ord-28c01d507c39412abc319815ad97c23d
Source dataset
uspto-grants-1999_11
Patent number
US05986096

Reaction notes

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