Benzyl Alcohol → HCID 10130617, compound

HRID 1838960Notes

Reaction equation

[Na].[CH2:2]([OH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[C:13]([NH2:18])[N:12]=1>>[NH2:10][C:11]1[N:16]=[C:15]([O:9][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:14]=[C:13]([NH2:18])[N:12]=1

Participants

Reactant 3

HCID 244Benzyl Alcohol

HCID 674322,4-Diamino-6-chloropyrimidine

HCID 5360545Sodium

Product 1

HCID 10130617HCID 10130617, compoundYield 62%

Conditions

Temperature: 150 °C

Procedure

Sodium (0.41 g, 17.8 mmol) was added to benzyl alcohol (15 ml) under a nitrogen atmosphere and the mixture was heated at 150° C. for 1.5 h. 2,6-Diamino-4-chloropyrimidine (2.16 g, 14.94 mmol) was added and the reaction mixture was stired at 180° C. for a further 2 h. Volatiles were removed in vacuo and the resulting residue was chromatographed on silia with dichloromethane: methanol (9:1) as eluent, to yield the title product as a white solid (1.98 g, 62%); νmax/cm−1 3347 (NH), 1498 (C6H5), 1608 (C6H5); δH (200 MHz, d6-DMSO) 5.20 (1H, s, C(5)H), 5.32 (2H, s, OCH2), 6.05 (2H, br s, NH2), 6.17 (2H, br s, NH2), 7.41-7.48 (5H, m, C6H5); m/z (+EI) 216 (M+, 100%), 139 (M+-C6H5, 33), 91 (94).

Workup

customVolatiles were removed in vacuo
customthe resulting residue was chromatographed on silia with dichloromethane: methanol (9:1) as eluent

Sources & evidence

ORD record: ord-e2e6a7779f584a73ad27ce25fc1f5424
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677345B1

Reaction notes

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